US3853926A - 17{62 -hydroxy-16,16-dimethylester-4-en-3-one - Google Patents
17{62 -hydroxy-16,16-dimethylester-4-en-3-one Download PDFInfo
- Publication number
- US3853926A US3853926A US00364340A US36434073A US3853926A US 3853926 A US3853926 A US 3853926A US 00364340 A US00364340 A US 00364340A US 36434073 A US36434073 A US 36434073A US 3853926 A US3853926 A US 3853926A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- dimethylestr
- parts
- steroid
- mixture
- 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 - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
Definitions
- the antiandrogenic activity of the steroid of this invention is remarkable because the corresponding 16- monomethyl steroid, a compound prepared by the instant inventor a number of years ago as disclosed in Example 7 of US. Pat. No. 3,049,555, has the opposite biological effect: it is androgenic.
- the monomethyl steroid also promotes anabolism, a possibly complicating side-effect which the dimethyl steroid of this invention does not share.
- the antiandrogenic utility of l7,B-hydroxy-16,l6- dimethylestr-4-en-3-one is evident from the results of a test for its capacity to inhibit the testosteronestimulated growth of seminal vesicle and prostate glands in castrated immature male rats.
- the procedure is as follows: 20 male Charles River rats are castrated at 22 days of age and separated into 2 equal groups such that for each animal in each group there is a littermate in the other. When the rats areabout 36 days old, an implant consisting of a mixture of 8 mg. of testosterone, 8 mg. of Carbowax (polyethylene glycol), and 16 mg.
- Flexo Wax C Light non-crystalline hydrocarbon wax melting at 6064 C.
- the compound to be tested dissolved or suspended in sesame oil, corn oil, or other physiologically inert vehicle is administered subcutaneously to each animal in one group at a dose of 10 mg. per kg. .daily for 24 successive days.
- the quantity of vehicle is such that a l-gm. rat receives approximately 0.1 ml. at the beginning of the test and with increasing body weight approximately 0.2 ml. at the end.
- Each animal in the second group receives concurrent subcutaneous daily injections of vehicle likewise adjusted to body weight, and these animals serve as controls.
- a compound is considered antiandrogenic if the mean weight of the vesicles in the group of nimalaflsatssilhs[@WfihifiiiflifiQflQflY .0 g (101) less than the corresponding weight in the control group and there is a proportionate decrease in the mean prostate weight for treats vis-a-vis controls. l7B-Hydroxyl6,16-dimethylestr-4-en-3-one was active in this test.
- the steroid of this invention can be administered in dosage unit form including, but not necessarily limited to, sterile solutions or suspensions for intramuscular injection, intravaginal or rectal compositions such as suppositories, lozenges for sublingual administration, and salves or lotions (including sprayable solutions or mixtures) for topical application.
- the appropriate dose in any given instance depends upon the nature of the condition treated and its severity, the route of administration, the species of mammal involved and its size and individual idiosyncrasies, etc. In general, and insofar as consistent with such factors,
- daily parenteral dosages of from 1 to about 5 mg. per
- EXAMPLE 1 Preparation of sterile solution A sterile solution containing mg. per ml. of 173- hydroxy-l6,16-dimethylestr-4-en-3-one is prepared by dissolving 10 gm. thereof in 50 ml. of benzyl alcohol, diluting to 1 l. with polyethylene glycol 400, and then filtering to remove microorganisms.
- EXAMPLE 2 Preparation of sterile suspension A sterile suspension is prepared by mixing 100 gm. of sorbitol with 30 mg. of polyethylene glycol 400 and 4 mg. of benzyl alcohol, whereupon sterilization is effected by filtration and to the filtrate is added 250 mg.
- EXAMPLE 4 EXAMPLE 5 Preparation of a salve A mixture of 15 parts of stearyl alcohol, 4 parts of cetyl alcohol, and 20 parts of polyethylene glycol 400 is melted, whereupon 10 parts of 17B-hydroxy-l6,16-
- compositions adapted to topical application comprise fatty alcohols, fatty acids, liquid petrolatum, glycerol monostearate, glycerol, propylene glycol and other polyalcohols, ethylene glycol polymers, surfactants, vegetable oils, fats, esters of fatty acids and fatty alcohols, water, and hydrous or anhydrous emulsion bases or gels.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Dental Preparations (AREA)
- Detergent Compositions (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fats And Perfumes (AREA)
Priority Applications (22)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00364340A US3853926A (en) | 1973-05-29 | 1973-05-29 | 17{62 -hydroxy-16,16-dimethylester-4-en-3-one |
ZA00743304A ZA743304B (en) | 1973-05-29 | 1974-05-22 | 17beta-hydroxy-16,16-dimethylestr-4-en-3-one |
AU69454/74A AU478213B2 (en) | 1973-05-29 | 1974-05-28 | 17b- hydroxy-16, 16-dimethylester-4-en-3-one |
IE1123/74A IE39292B1 (en) | 1973-05-29 | 1974-05-28 | 17 hydroxy 16,16-dimethylestr-4-en-3-one |
BE144827A BE815626A (fr) | 1973-05-29 | 1974-05-28 | Hydroxy-17beta-dimethyl-16,16 4-oestrenone-3 et procede de sa preparation |
CA200,995A CA1033716A (en) | 1973-05-29 | 1974-05-28 | 17.beta.-HYDROXY-16,16-DIMETHYLESTR-4-EN-3-ONE |
HUSE1731A HU168555B (de) | 1973-05-29 | 1974-05-28 | |
ES426711A ES426711A1 (es) | 1973-05-29 | 1974-05-28 | Procedimiento para la preparacion de 17b-hidroxi-16,16-di- metilester-4en-3-ona. |
DK289274A DK132328C (da) | 1973-05-29 | 1974-05-28 | Analogifremgangsmade til fremstilling af 17beta-hydroxy-16,16-dimethylestr-4-en-3-on |
AT438674A AT333990B (de) | 1973-05-29 | 1974-05-28 | Verfahren zur herstellung des neuen 17beta-hydroxy-16,16-dimethylostr-4-en-3-ons |
GB2351174A GB1416839A (en) | 1973-05-29 | 1974-05-28 | 17beta-hydroxy-16,16-dimethylestr-4-en-3-one |
PH15876A PH10428A (en) | 1973-05-29 | 1974-05-28 | 17beta-hydroxy-16-dimethlester-4-en-3-one |
JP49060202A JPS5019745A (de) | 1973-05-29 | 1974-05-28 | |
FR7418471A FR2231383B1 (de) | 1973-05-29 | 1974-05-28 | |
SE7407031A SE401835B (sv) | 1973-05-29 | 1974-05-28 | Forfarande for framstellning av 17beta-hydroxi-16,16-dimetylest-4-en-3-on |
NO741929A NO140104C (no) | 1973-05-29 | 1974-05-28 | Analogifremgangsmaate til fremstilling av 17beta-hydroksy-16,16-dimetylestr-4-en-3-on med terapeutisk aktivitet |
FI1632/74A FI53218C (de) | 1973-05-29 | 1974-05-28 | |
IL44903A IL44903A (en) | 1973-05-29 | 1974-05-28 | 71 - Hydroxy - 61, 61 - Dimethiester - 4 - An - 3 - On, its preparation and pharmaceutical preparations containing it |
DE19742425822 DE2425822A1 (de) | 1973-05-29 | 1974-05-28 | 17 beta-hydroxy-16,16-dimethyloestr-4en-3-on und verfahren zur herstellung desselben |
NL7407122A NL7407122A (de) | 1973-05-29 | 1974-05-28 | |
AR253974A AR199619A1 (es) | 1973-05-29 | 1974-05-29 | Un procedimiento para preparar 17beta-hidroxi-16,16-dimetilestr-4-en 3-ona |
CH735574A CH609705A5 (de) | 1973-05-29 | 1974-05-29 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00364340A US3853926A (en) | 1973-05-29 | 1973-05-29 | 17{62 -hydroxy-16,16-dimethylester-4-en-3-one |
Publications (1)
Publication Number | Publication Date |
---|---|
US3853926A true US3853926A (en) | 1974-12-10 |
Family
ID=23434065
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00364340A Expired - Lifetime US3853926A (en) | 1973-05-29 | 1973-05-29 | 17{62 -hydroxy-16,16-dimethylester-4-en-3-one |
Country Status (21)
Country | Link |
---|---|
US (1) | US3853926A (de) |
JP (1) | JPS5019745A (de) |
AR (1) | AR199619A1 (de) |
AT (1) | AT333990B (de) |
BE (1) | BE815626A (de) |
CA (1) | CA1033716A (de) |
CH (1) | CH609705A5 (de) |
DE (1) | DE2425822A1 (de) |
DK (1) | DK132328C (de) |
ES (1) | ES426711A1 (de) |
FI (1) | FI53218C (de) |
FR (1) | FR2231383B1 (de) |
GB (1) | GB1416839A (de) |
HU (1) | HU168555B (de) |
IE (1) | IE39292B1 (de) |
IL (1) | IL44903A (de) |
NL (1) | NL7407122A (de) |
NO (1) | NO140104C (de) |
PH (1) | PH10428A (de) |
SE (1) | SE401835B (de) |
ZA (1) | ZA743304B (de) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2610497A1 (de) * | 1975-03-21 | 1976-10-07 | Beecham Group Ltd | In 16-stellung disubstituierte 3- ketosteroide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
EP0028525A2 (de) * | 1979-10-31 | 1981-05-13 | Orion-Yhtymä Oy | Behandlungsmittel zur Verbesserung des Haarwuchses und Verhütung von Kopfschuppen |
US6355686B1 (en) * | 2000-06-30 | 2002-03-12 | Unilever Home And Personal Care Usa, Division Of Conopco, Inc. | Cosmetic compositions containing substituted amine derivatives |
US6355687B1 (en) * | 2000-06-30 | 2002-03-12 | Unilever Home And Personal Care Usa, Division Of Conopco, Inc. | Cosmetic compositions containing substituted iminodibenzyl or fluorene derivatives |
US6372795B1 (en) * | 2000-06-30 | 2002-04-16 | Unilever Home And Personal Care Usa, A Division Of Conopco, Inc. | Cosmetic compositions containing substituted amide derivatives |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9021546D0 (en) * | 1990-10-04 | 1990-11-21 | Beecham Group Plc | Novel composition |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3049555A (en) * | 1959-12-22 | 1962-08-14 | Searle & Co | 3-alkoxy-16-methyl-1, 3, 5 (10)-estratrien-17-ones |
US3280156A (en) * | 1965-10-13 | 1966-10-18 | Searle & Co | 17beta-hydroxyspiro(estr-4-ene-16, 1'-cyclopropan)-3-ones |
-
1973
- 1973-05-29 US US00364340A patent/US3853926A/en not_active Expired - Lifetime
-
1974
- 1974-05-22 ZA ZA00743304A patent/ZA743304B/xx unknown
- 1974-05-28 CA CA200,995A patent/CA1033716A/en not_active Expired
- 1974-05-28 SE SE7407031A patent/SE401835B/xx unknown
- 1974-05-28 PH PH15876A patent/PH10428A/en unknown
- 1974-05-28 IE IE1123/74A patent/IE39292B1/xx unknown
- 1974-05-28 FI FI1632/74A patent/FI53218C/fi active
- 1974-05-28 FR FR7418471A patent/FR2231383B1/fr not_active Expired
- 1974-05-28 DE DE19742425822 patent/DE2425822A1/de not_active Withdrawn
- 1974-05-28 HU HUSE1731A patent/HU168555B/hu unknown
- 1974-05-28 AT AT438674A patent/AT333990B/de not_active IP Right Cessation
- 1974-05-28 DK DK289274A patent/DK132328C/da active
- 1974-05-28 BE BE144827A patent/BE815626A/xx unknown
- 1974-05-28 IL IL44903A patent/IL44903A/en unknown
- 1974-05-28 GB GB2351174A patent/GB1416839A/en not_active Expired
- 1974-05-28 NO NO741929A patent/NO140104C/no unknown
- 1974-05-28 JP JP49060202A patent/JPS5019745A/ja active Pending
- 1974-05-28 NL NL7407122A patent/NL7407122A/xx not_active Application Discontinuation
- 1974-05-28 ES ES426711A patent/ES426711A1/es not_active Expired
- 1974-05-29 CH CH735574A patent/CH609705A5/xx not_active IP Right Cessation
- 1974-05-29 AR AR253974A patent/AR199619A1/es active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3049555A (en) * | 1959-12-22 | 1962-08-14 | Searle & Co | 3-alkoxy-16-methyl-1, 3, 5 (10)-estratrien-17-ones |
US3280156A (en) * | 1965-10-13 | 1966-10-18 | Searle & Co | 17beta-hydroxyspiro(estr-4-ene-16, 1'-cyclopropan)-3-ones |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2610497A1 (de) * | 1975-03-21 | 1976-10-07 | Beecham Group Ltd | In 16-stellung disubstituierte 3- ketosteroide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
EP0028525A2 (de) * | 1979-10-31 | 1981-05-13 | Orion-Yhtymä Oy | Behandlungsmittel zur Verbesserung des Haarwuchses und Verhütung von Kopfschuppen |
EP0028525A3 (de) * | 1979-10-31 | 1981-10-28 | Orion-Yhtymä Oy | Behandlungsmittel zur Verbesserung des Haarwuchses und Verhütung von Kopfschuppen |
US6355686B1 (en) * | 2000-06-30 | 2002-03-12 | Unilever Home And Personal Care Usa, Division Of Conopco, Inc. | Cosmetic compositions containing substituted amine derivatives |
US6355687B1 (en) * | 2000-06-30 | 2002-03-12 | Unilever Home And Personal Care Usa, Division Of Conopco, Inc. | Cosmetic compositions containing substituted iminodibenzyl or fluorene derivatives |
US6372795B1 (en) * | 2000-06-30 | 2002-04-16 | Unilever Home And Personal Care Usa, A Division Of Conopco, Inc. | Cosmetic compositions containing substituted amide derivatives |
Also Published As
Publication number | Publication date |
---|---|
IE39292B1 (en) | 1978-09-13 |
FI163274A (de) | 1974-11-30 |
FR2231383A1 (de) | 1974-12-27 |
NO140104B (no) | 1979-03-26 |
NO140104C (no) | 1979-07-11 |
DE2425822A1 (de) | 1975-01-02 |
FI53218C (de) | 1978-03-10 |
SE7407031L (de) | 1974-12-02 |
AR199619A1 (es) | 1974-09-13 |
JPS5019745A (de) | 1975-03-01 |
HU168555B (de) | 1976-05-28 |
FI53218B (de) | 1977-11-30 |
GB1416839A (en) | 1975-12-10 |
ATA438674A (de) | 1976-04-15 |
DK132328C (da) | 1976-05-31 |
DK289274A (de) | 1975-01-13 |
CH609705A5 (de) | 1979-03-15 |
ES426711A1 (es) | 1976-08-01 |
IE39292L (en) | 1974-11-29 |
ZA743304B (en) | 1976-01-28 |
DK132328B (da) | 1975-11-24 |
IL44903A0 (en) | 1974-07-31 |
SE401835B (sv) | 1978-05-29 |
CA1033716A (en) | 1978-06-27 |
IL44903A (en) | 1977-05-31 |
AT333990B (de) | 1976-12-27 |
PH10428A (en) | 1977-03-16 |
AU6945474A (en) | 1975-12-04 |
NL7407122A (de) | 1974-12-03 |
FR2231383B1 (de) | 1977-11-04 |
BE815626A (fr) | 1974-11-28 |
NO741929L (no) | 1974-12-02 |
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