US3853926A - 17{62 -hydroxy-16,16-dimethylester-4-en-3-one - Google Patents

17{62 -hydroxy-16,16-dimethylester-4-en-3-one Download PDF

Info

Publication number: US3853926A
Authority: US; United States
Prior art keywords: hydroxy; dimethylestr; parts; steroid; mixture
Prior art date: 1973-05-29
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

Application number

US00364340A

Other languages

English (en)

Inventor

D Tyner

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.)

GD Searle LLC

Original Assignee

GD Searle LLC

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.)

1973-05-29

Filing date

1973-05-29

Publication date

1974-12-10

1973-05-29 Application filed by GD Searle LLC filed Critical GD Searle LLC

1973-05-29 Priority to US00364340A priority Critical patent/US3853926A/en

1974-05-22 Priority to ZA00743304A priority patent/ZA743304B/xx

1974-05-28 Priority to FI1632/74A priority patent/FI53218C/fi

1974-05-28 Priority to NL7407122A priority patent/NL7407122A/xx

1974-05-28 Priority to IE1123/74A priority patent/IE39292B1/xx

1974-05-28 Priority to GB2351174A priority patent/GB1416839A/en

1974-05-28 Priority to SE7407031A priority patent/SE401835B/xx

1974-05-28 Priority to FR7418471A priority patent/FR2231383B1/fr

1974-05-28 Priority to HUSE1731A priority patent/HU168555B/hu

1974-05-28 Priority to PH15876A priority patent/PH10428A/en

1974-05-28 Priority to IL44903A priority patent/IL44903A/en

1974-05-28 Priority to ES426711A priority patent/ES426711A1/es

1974-05-28 Priority to NO741929A priority patent/NO140104C/no

1974-05-28 Priority to DK289274A priority patent/DK132328C/da

1974-05-28 Priority to JP49060202A priority patent/JPS5019745A/ja

1974-05-28 Priority to AT438674A priority patent/AT333990B/de

1974-05-28 Priority to AU69454/74A priority patent/AU478213B2/en

1974-05-28 Priority to BE144827A priority patent/BE815626A/xx

1974-05-28 Priority to CA200,995A priority patent/CA1033716A/en

1974-05-28 Priority to DE19742425822 priority patent/DE2425822A1/de

1974-05-29 Priority to CH735574A priority patent/CH609705A5/xx

1974-05-29 Priority to AR253974A priority patent/AR199619A1/es

1974-12-10 Application granted granted Critical

1974-12-10 Publication of US3853926A publication Critical patent/US3853926A/en

1991-12-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 abstract description 7
230000002280 anti-androgenic effect Effects 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 5
230000002086 anti-sebum Effects 0.000 abstract description 3
JYCITEUSLNKPHC-URNBORRASA-N metogest Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC(C)(C)[C@H](O)[C@@]1(C)CC2 JYCITEUSLNKPHC-URNBORRASA-N 0.000 abstract 1
239000000203 mixture Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
210000002307 prostate Anatomy 0.000 description 5
239000000243 solution Substances 0.000 description 5
150000003431 steroids Chemical class 0.000 description 5
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000000829 suppository Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229940068918 polyethylene glycol 400 Drugs 0.000 description 3
239000008174 sterile solution Substances 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
230000001548 androgenic effect Effects 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000003925 fat Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
239000007943 implant Substances 0.000 description 2
-1 monomethyl steroid Chemical class 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
239000011369 resultant mixture Substances 0.000 description 2
210000001625 seminal vesicle Anatomy 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
201000010653 vesiculitis Diseases 0.000 description 2
WONHBFGPUTVACG-MDMHHNQBSA-N CC([C@@]12CCC[C@H]1[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)=O)C Chemical compound CC([C@@]12CCC[C@H]1[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)=O)C WONHBFGPUTVACG-MDMHHNQBSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000000034 method Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000465 moulding Methods 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
239000002547 new drug Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000002374 sebum Anatomy 0.000 description 1
230000028327 secretion Effects 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229960001124 trientine Drugs 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

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
- 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
- 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

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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Dental Preparations (AREA)
Detergent Compositions (AREA)
Medicinal Preparation (AREA)
Fats And Perfumes (AREA)

US00364340A 1973-05-29 1973-05-29 17{62 -hydroxy-16,16-dimethylester-4-en-3-one Expired - Lifetime US3853926A (en)

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
DK289274A DK132328C (da)	1973-05-29	1974-05-28	Analogifremgangsmade til fremstilling af 17beta-hydroxy-16,16-dimethylestr-4-en-3-on
IE1123/74A IE39292B1 (en)	1973-05-29	1974-05-28	17 hydroxy 16,16-dimethylestr-4-en-3-one
GB2351174A GB1416839A (en)	1973-05-29	1974-05-28	17beta-hydroxy-16,16-dimethylestr-4-en-3-one
SE7407031A SE401835B (sv)	1973-05-29	1974-05-28	Forfarande for framstellning av 17beta-hydroxi-16,16-dimetylest-4-en-3-on
FR7418471A FR2231383B1 (de)	1973-05-29	1974-05-28
HUSE1731A HU168555B (de)	1973-05-29	1974-05-28
PH15876A PH10428A (en)	1973-05-29	1974-05-28	17beta-hydroxy-16-dimethlester-4-en-3-one
IL44903A IL44903A (en)	1973-05-29	1974-05-28	17beta-hydroxy-16,16-dimethylestr-4-en-3-one its preparation and pharmaceutical compositions containing it
FI1632/74A FI53218C (de)	1973-05-29	1974-05-28
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
NL7407122A NL7407122A (de)	1973-05-29	1974-05-28
JP49060202A JPS5019745A (de)	1973-05-29	1974-05-28
AT438674A AT333990B (de)	1973-05-29	1974-05-28	Verfahren zur herstellung des neuen 17beta-hydroxy-16,16-dimethylostr-4-en-3-ons
AU69454/74A AU478213B2 (en)	1973-05-29	1974-05-28	17b- hydroxy-16, 16-dimethylester-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
DE19742425822 DE2425822A1 (de)	1973-05-29	1974-05-28	17 beta-hydroxy-16,16-dimethyloestr-4en-3-on und verfahren zur herstellung desselben
ES426711A ES426711A1 (es)	1973-05-29	1974-05-28	Procedimiento para la preparacion de 17b-hidroxi-16,16-di- metilester-4en-3-ona.
CH735574A CH609705A5 (de)	1973-05-29	1974-05-29
AR253974A AR199619A1 (es)	1973-05-29	1974-05-29	Un procedimiento para preparar 17beta-hidroxi-16,16-dimetilestr-4-en 3-ona

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)

* Cited by examiner, † Cited by third party
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
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

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9021546D0 (en) *	1990-10-04	1990-11-21	Beecham Group Plc	Novel composition

Citations (2)

* Cited by examiner, † Cited by third party
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 DE DE19742425822 patent/DE2425822A1/de not_active Withdrawn
- 1974-05-28 ES ES426711A patent/ES426711A1/es not_active Expired
- 1974-05-28 IE IE1123/74A patent/IE39292B1/xx unknown
- 1974-05-28 PH PH15876A patent/PH10428A/en unknown
- 1974-05-28 FI FI1632/74A patent/FI53218C/fi active
- 1974-05-28 DK DK289274A patent/DK132328C/da active
- 1974-05-28 NL NL7407122A patent/NL7407122A/xx not_active Application Discontinuation
- 1974-05-28 NO NO741929A patent/NO140104C/no unknown
- 1974-05-28 GB GB2351174A patent/GB1416839A/en not_active Expired
- 1974-05-28 BE BE144827A patent/BE815626A/xx unknown
- 1974-05-28 HU HUSE1731A patent/HU168555B/hu unknown
- 1974-05-28 JP JP49060202A patent/JPS5019745A/ja active Pending
- 1974-05-28 IL IL44903A patent/IL44903A/en unknown
- 1974-05-28 SE SE7407031A patent/SE401835B/xx unknown
- 1974-05-28 CA CA200,995A patent/CA1033716A/en not_active Expired
- 1974-05-28 FR FR7418471A patent/FR2231383B1/fr not_active Expired
- 1974-05-28 AT AT438674A patent/AT333990B/de not_active IP Right Cessation
- 1974-05-29 CH CH735574A patent/CH609705A5/xx not_active IP Right Cessation
- 1974-05-29 AR AR253974A patent/AR199619A1/es active

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US3280156A (en) *	1965-10-13	1966-10-18	Searle & Co	17beta-hydroxyspiro(estr-4-ene-16, 1'-cyclopropan)-3-ones

Cited By (5)

* Cited by examiner, † Cited by third party
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
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
JPS5019745A (de)	1975-03-01
SE401835B (sv)	1978-05-29
DK289274A (de)	1975-01-13
ATA438674A (de)	1976-04-15
IE39292L (en)	1974-11-29
CA1033716A (en)	1978-06-27
FR2231383B1 (de)	1977-11-04
IL44903A (en)	1977-05-31
FI53218C (de)	1978-03-10
GB1416839A (en)	1975-12-10
IE39292B1 (en)	1978-09-13
FI53218B (de)	1977-11-30
PH10428A (en)	1977-03-16
CH609705A5 (de)	1979-03-15
SE7407031L (de)	1974-12-02
DK132328C (da)	1976-05-31
AR199619A1 (es)	1974-09-13
HU168555B (de)	1976-05-28
DE2425822A1 (de)	1975-01-02
NL7407122A (de)	1974-12-03
ES426711A1 (es)	1976-08-01
NO140104B (no)	1979-03-26
AT333990B (de)	1976-12-27
NO741929L (no)	1974-12-02
NO140104C (no)	1979-07-11
IL44903A0 (en)	1974-07-31
DK132328B (da)	1975-11-24
BE815626A (fr)	1974-11-28
FI163274A7 (de)	1974-11-30
FR2231383A1 (de)	1974-12-27
AU6945474A (en)	1975-12-04
ZA743304B (en)	1976-01-28

Publication	Publication Date	Title
Murakami	1986	Development of the os penis in genital tubercles cultured beneath the renal capsule of adult rats
BOAS et al.	1950	The mechanism of estrogen inhibition of comb growth in the cockerel, with histologic observations
DE2818164A1 (de)	1979-10-31	1,3-dibenzoesaeureester des 17alpha- ethinyl-7 alpha -methyl-1,3,5(10)-oestratrien- 1,3,17 beta -triols, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen
Parkes et al.	1944	Effect of androgens and estrogens on birds
Stefano et al.	1964	Hypophyso-adrenal regulation of moulting in the toad
IL44903A (en)	1977-05-31	17beta-hydroxy-16,16-dimethylestr-4-en-3-one its preparation and pharmaceutical compositions containing it
US4381298A (en)	1983-04-26	Oral male contraceptive composition
Robson et al.	1931	Pregnancy Changes in the Rabbit's Uterus and their Relation to Endocrine Activity
Zeilmaker	1964	Aspects of the regulation of corpus luteum function in androgen-sterilized female rats
Kumaran et al.	1949	The Endocrinology of Spermatogenesis in Birds: I. Effect of Estrogen and Androgen
Horning	1958	Carcinogenic action of androgens
US3939265A (en)	1976-02-17	Novel zootechnical compositions
Koch	1938	The chemistry and biology of male sex hormones
US3032469A (en)	1962-05-01	Long acting steroid compounds
KR790001897B1 (ko)	1979-12-27	17β-히드록시-16,16-디메틸에스트르-4-엔-3-온의 제조방법
US3186907A (en)	1965-06-01	19-nor-testosterone derivatives, their process of preparation and their method of utilization
Revesz et al.	1967	Hormonal and biological activities of 3β, 17α-diacetoxy-6-chloropregna-4, 6-diene-20-one
US3919267A (en)	1975-11-11	13{62 -ethyl-17{60 -methyl-18,19-dinor-{66 {hu 4,9{b -pregnadiene-3,20-dione
Kincl et al.	1965	The biological activity of estrogen-free norethindrone
Iglesias et al.	1956	The influence of the gonads and of certain steroid hormones on the growth of the spontaneous and transplantable ovarian tumor in AXC rats
US3240671A (en)	1966-03-15	Therapeutic composition containing the 3-cyclopentyl enol ether of 17alpha-acetoxy progesterone and method of using the same
US3547959A (en)	1970-12-15	Novel delta**4,9-pregnadiene
US3574690A (en)	1971-04-13	Delta 4,9,11-gonatriene-3-ones
Wada et al.	1963	Influence of Progesterone, Estradiol Benzoate, and Relaxin upon Placentomata Formation in Mice.
Rubinstein et al.	1939	Effect of anterior pituitary extract on spermatogenesis in rat

US3853926A - 17{62 -hydroxy-16,16-dimethylester-4-en-3-one - Google Patents

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