WO1988008295A1 - Hair growth inhibition using substitued amidines or guanidines - Google Patents
Hair growth inhibition using substitued amidines or guanidines Download PDFInfo
- Publication number
- WO1988008295A1 WO1988008295A1 PCT/US1988/000400 US8800400W WO8808295A1 WO 1988008295 A1 WO1988008295 A1 WO 1988008295A1 US 8800400 W US8800400 W US 8800400W WO 8808295 A1 WO8808295 A1 WO 8808295A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- adamantyl
- morpholinecarboxamidine
- cyclohexyl
- compound
- growth
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
- A61Q7/02—Preparations for inhibiting or slowing hair growth
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/43—Guanidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
Definitions
- the present invention provides a new use for known compositions of matter. More particularly, the present invention provides topical compositions and a method for inhibiting hair growth with substituted amidines or guanidines of the Formula I.
- Adamantyl containing guanidines are known, as disclosed in U.S. Patent 4,007,181. These compounds are useful for antiarrhythmic and diuretic uses.
- the present invention particularly provides a topical composition for inhibiting the growth of mammalian hair comprising a compound of the Formula I, wherein R 1 and R 2 are the same or different and are
- R 3 and R 4 when taken together with the nitrogen to which they are attached form a saturated heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, hexamethyleneimino, piperazino, N-alkylpiperazino wherein the alkyl portion of the moiety is from 1 to 3 carbon atoms, inclusive, morpholino, or thiomorpholino and a vehicle adapted for topical application;
- R 3 and R 4 when taken together with the nitrogen to which they are attached form a saturated heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, hexamethyleneimino, piperazino, N-alkylpiperazino wherein the alkyl portion of the moiety is from 1 to 3 carbon atoms, inclusive, morpholino, or thiomorpholino and a vehicle adapted for topical application, in an amount effective to inhibit the growth of mammalian hair.
- a saturated heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, hexamethyleneimino, piperazino, N-alkylpiperazino wherein the alkyl portion of the moiety is from 1 to 3 carbon atoms, inclusive, morpholino, or thiomorpholino and a vehicle adapted for topical application, in an amount effective to inhibit the growth of mammalian hair.
- Formulations for topical administration of the compounds of the present invention contain the compounds in a range of from 0.1 to 2.5% by weight of the compound. Such formulations are topically administered, daily, e.g., from 1 to 2 times daily.
- the present invention provides treatment of various mammalian species, including humans.
- Topical administration of the compositions of the present invention to mammals, including humans is readily undertaken by a physician or veterinarian of ordinary skill in the art.
- N,N-di-2-adamantyl-4-morpholinecarboxamidine Most preferred is N-1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine.
- Example 1 Four solutions containing 1.25, 2.5, 5.0 and 10% by weight of N- 1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine were applied to the skin of shaved rats. The 5 and 10% solution caused skin rashes and loss of body weight and the studies on these animals were discontinued. The best results were obtained with a 2.5% solution which was topically applied once a day for seven days. Hair growth ceased in the animals during treatment, but when the drug was discontinued, hair growth resumed.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides novel compositions and methods for inhibiting hair growth using adamantyl containing guanidines.
Description
HAIR GROWTH INHIBITION USING SUBSTITUTED AMIDINES OR GUANIDINES BACKGROUND OF THE INVENTION
The present invention provides a new use for known compositions of matter. More particularly, the present invention provides topical compositions and a method for inhibiting hair growth with substituted amidines or guanidines of the Formula I.
Adamantyl containing guanidines are known, as disclosed in U.S. Patent 4,007,181. These compounds are useful for antiarrhythmic and diuretic uses.
Numerous compounds which remove unwanted hair are known. However, the present invention provides compounds which inhibit the growth of hair in unwanted areas. INFORMATION DISCLOSURE Adamantyl containing guanidines are known as disclosed in U.S. Patent 4,007,181. SUMMARY OF THE INVENTION
The present invention particularly provides a topical composition for inhibiting the growth of mammalian hair comprising a compound of the Formula I, wherein R1 and R2 are the same or different and are
(a) adamantyl or a cycloalkyl of 5 to 7 carbon atoms, inclusive;
(b) R3 and R4 when taken together with the nitrogen to which they are attached form a saturated heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, hexamethyleneimino, piperazino, N-alkylpiperazino wherein the alkyl portion of the moiety is from 1 to 3 carbon atoms, inclusive, morpholino, or thiomorpholino and a vehicle adapted for topical application;
2) a method for inhibiting the growth of mammalian hair comprising the topical application of a compound of the Formula I, wherein R1 and R2 are the same or different and are
(a) adamantyl or a cycloalkyl of 5 to 7 carbon atoms, inclusive;
(b) R3 and R4 when taken together with the nitrogen to which they are attached form a saturated heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, hexamethyleneimino, piperazino, N-alkylpiperazino wherein the alkyl portion of the moiety is from 1 to 3 carbon atoms, inclusive, morpholino, or thiomorpholino and a vehicle adapted for topical application, in an amount effective
to inhibit the growth of mammalian hair.
Compounds of Formula I are made and prepared according to U.S. Patent 4,007,181, which is expressly incorporated by reference herein. Suitable topical formulations of these compounds are disclosed in U.S. Patents 4,139,619 and 4,596,812, which are expressly incorporated by reference herein.
Formulations for topical administration of the compounds of the present invention contain the compounds in a range of from 0.1 to 2.5% by weight of the compound. Such formulations are topically administered, daily, e.g., from 1 to 2 times daily.
The present invention provides treatment of various mammalian species, including humans. Topical administration of the compositions of the present invention to mammals, including humans is readily undertaken by a physician or veterinarian of ordinary skill in the art.
Preparation of topical compositions of the compounds of the present invention is easily accomplished using known means . Those of ordinary skill in the pharmaceutical arts could readily prepare topical compositions of these compounds based on the disclosures of the U.S. patents incorporated by reference herein.
Certain of the compounds of the present invention are preferred.
N-1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine;
N-1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine hydrochloride;
N,N'-di-1-adamantyl-4-morpholinecarboxamidine;
N,N-di-1-adamantyl-4-morpholinecarboxamidine hydrochloride; and
N,N-di-2-adamantyl-4-morpholinecarboxamidine. Most preferred is N-1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention is seen more fully by the example given below. Example 1 Four solutions containing 1.25, 2.5, 5.0 and 10% by weight of N- 1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine were applied to the skin of shaved rats. The 5 and 10% solution caused skin rashes and loss of body weight and the studies on these animals were
discontinued. The best results were obtained with a 2.5% solution which was topically applied once a day for seven days. Hair growth ceased in the animals during treatment, but when the drug was discontinued, hair growth resumed.
Claims
CLAIMS 1. A topical composition for inhibiting the growth of mammalian hair comprising a compound of the Formula I
(a) adamantyl or a cycloalkyl of 5 to 7 carbon atoms, inclusive;
(b) R3 and R4 when taken together with the nitrogen to which they are attached form a saturated heterocyclic ring selected from the roup consisting of pyrrolidino, piperidino, hexamethyleneimino, piperazino, N-alkylpiperazino wherein the alkyl portion of the moiety is from 1 to 3 carbon atoms, inclusive, morpholino, or thiomorpholino; and a vehicle adapted for topical application.
2. A method for inhibiting the growth of mammalian hair comprising the topical application of an amount effective to inhibit hair growth of a compound of the Formula I, wherein R1 and R2 are the same or different and are (a) adamantyl or a cycloalkyl of 5 to 7 carbon atoms, inclusive;
(b) R3 and R4 when taken together with the nitrogen to which they are attached form a saturated heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, hexamethyleneimino, piperazino, N-alkylpiperazino wherein the alkyl portion of the moiety is from 1 to 3 carbon atoms, inclusive, morpholino, or thiomorpholino and a vehicle adapted for topical application, in an amount effective to inhibit the growth of mammalian hair.
3. A composition of Claim 1 containing a compound selected from the group consisting of
N-1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine; N-1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine hydrochloride;
N,N'-di-1-adamantyl-4 -morpholinecarboxamidine; N,N-di-1-adamantyl-4-morpholinecarboxamidine hydrochloride; and N,N-di-2-adamantyl-4-morpho1inecarboxamidine.
4. A method of Claim 2 containing a compound selected from the group consisting of
N-1-adamantyl-N'-eyelohexyl-4-morpholinecarboxamidine; N-1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine hydrochloride; N,N'-di-1-adamantyl-4-morρholinecarboxamidine;
N,N-di-1-adamantyl-4-morpholinecarboxamidine hydrochloride; and N,N-di-2-adamantyl-4-morpholinecarboxamidine.
5. A composition of Claim 3, wherein the compound is N-1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine.
6. A method of Claim 4, wherein the compound is N-1-adamantyl-N'-cyclohexyl-4-morpholinecarboxamidine.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4170887A | 1987-04-23 | 1987-04-23 | |
US041,708 | 1987-04-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1988008295A1 true WO1988008295A1 (en) | 1988-11-03 |
Family
ID=21917920
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1988/000400 WO1988008295A1 (en) | 1987-04-23 | 1988-02-17 | Hair growth inhibition using substitued amidines or guanidines |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU1368888A (en) |
WO (1) | WO1988008295A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0532219A2 (en) * | 1991-09-04 | 1993-03-17 | Unilever Plc | Cosmetic composition |
EP1477155A1 (en) * | 2003-05-16 | 2004-11-17 | The Procter & Gamble Company | Compositions comprising an amidine and an alkane polyol |
EP1477157A1 (en) * | 2003-05-16 | 2004-11-17 | The Procter & Gamble Company | Compositions comprising an amidine and an alkane polyol |
WO2010016606A2 (en) * | 2008-08-05 | 2010-02-11 | Kao Corporation | Hair growth regulating agent |
US9655833B2 (en) | 2009-07-29 | 2017-05-23 | Elise OLSEN | Compositions and methods for inhibiting hair growth |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4007181A (en) * | 1974-02-11 | 1977-02-08 | The Upjohn Company | Adamantyl containing guanidines |
EP0096521A2 (en) * | 1982-06-01 | 1983-12-21 | THE PROCTER & GAMBLE COMPANY | Depilatory compositions |
-
1988
- 1988-02-17 AU AU13688/88A patent/AU1368888A/en not_active Abandoned
- 1988-02-17 WO PCT/US1988/000400 patent/WO1988008295A1/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4007181A (en) * | 1974-02-11 | 1977-02-08 | The Upjohn Company | Adamantyl containing guanidines |
EP0096521A2 (en) * | 1982-06-01 | 1983-12-21 | THE PROCTER & GAMBLE COMPANY | Depilatory compositions |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0532219A2 (en) * | 1991-09-04 | 1993-03-17 | Unilever Plc | Cosmetic composition |
EP0532219A3 (en) * | 1991-09-04 | 1993-11-18 | Unilever Plc | Cosmetic composition |
US5378455A (en) * | 1991-09-04 | 1995-01-03 | Chesebrough-Ponds Usa Co., Division Of Conopco, Inc. | Cosmetic composition for inhibiting hair growth |
EP1477155A1 (en) * | 2003-05-16 | 2004-11-17 | The Procter & Gamble Company | Compositions comprising an amidine and an alkane polyol |
EP1477157A1 (en) * | 2003-05-16 | 2004-11-17 | The Procter & Gamble Company | Compositions comprising an amidine and an alkane polyol |
WO2004103290A2 (en) * | 2003-05-16 | 2004-12-02 | The Procter & Gamble Company | Compositions comprising an amidine and an alkane polyol |
WO2004103290A3 (en) * | 2003-05-16 | 2006-08-17 | Procter & Gamble | Compositions comprising an amidine and an alkane polyol |
WO2010016606A2 (en) * | 2008-08-05 | 2010-02-11 | Kao Corporation | Hair growth regulating agent |
WO2010016606A3 (en) * | 2008-08-05 | 2010-04-15 | Kao Corporation | Hair growth regulating agent |
US8440717B2 (en) | 2008-08-05 | 2013-05-14 | Kao Corporation | Hair growth regulating agent |
US9655833B2 (en) | 2009-07-29 | 2017-05-23 | Elise OLSEN | Compositions and methods for inhibiting hair growth |
US9707169B2 (en) | 2009-07-29 | 2017-07-18 | Elise OLSEN | Compositions and methods for inhibiting hair growth |
US10159634B2 (en) | 2009-07-29 | 2018-12-25 | Elise A. Olsen | Compositions and methods for inhibiting hair growth |
EP3871671A2 (en) | 2009-07-29 | 2021-09-01 | Olsen, Elise | Fp receptor antagonists for inhibiting hair growth |
Also Published As
Publication number | Publication date |
---|---|
AU1368888A (en) | 1988-12-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ATE98651T1 (en) | PEPTIDES WITH TACHYKIN ANTAGONIST ACTIVITY, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM. | |
MX9203744A (en) | WATER-Soluble CAMPTOTECHE ANALOGS USEFUL TO INHIBIT THE GROWTH OF ANIMAL TUMOR CELLS. | |
AU2983889A (en) | 3-alkenyl-1-azabicyclo {3.2.0} hept-2-ene-2-carboxylic acid compounds | |
KR930010039A (en) | Indolopyrrolocarbazole derivatives | |
KR880006193A (en) | Piperidine Compounds and Their Preparation and Uses | |
KR880003958A (en) | Novel cefem compound and preparation method thereof | |
US4820711A (en) | Method for treating actinic keratosis with cytotoxic agents | |
ATE61340T1 (en) | AMINO ACID DERIVATIVES AND THEIR PRODUCTION PROCESSES. | |
EP0220523A3 (en) | Novel quinolinecarboxylic acid compounds, processes for preparing them, pharmaceutical composition and use | |
WO1988008295A1 (en) | Hair growth inhibition using substitued amidines or guanidines | |
AU558261B2 (en) | Dialkylaminoalkyoxybenzylalcohol derivatives | |
IE832273L (en) | 7-substituted-3-vinyl-3-cephem compounds | |
EP0168921A3 (en) | Chemical compounds | |
SE8007171L (en) | PROCEDURE FOR PREPARING A PHARMACEUTICAL COMPOSITION INCLUDING SUBSTITUTED DIPHENYL SULPHIDS | |
AU634266B2 (en) | Cycloalkylene azoles, processes for their production and use,and pharmaceutical preparations obtained therefrom | |
KR890003378A (en) | Naphthyridine Compounds Having Antimicrobial Activity Against Anaerobic Bacteria | |
CA2104515C (en) | Composition for accelerating healing of wound | |
DE3668888D1 (en) | AN IMIDAZOLID INTRION DERIVATIVE OR A PHARMACEUTICAL COMPOSITION CONTAINING ITS PHARMACEUTICAL ACCEPTABLE SALTS. | |
EP0233745A3 (en) | Chemical compounds | |
KR900016210A (en) | New compounds | |
IE893258L (en) | New 2-carbonyl substituted n,n'-di-(trimethoxybenzoyl)¹piperazines, process for preparing the same and¹therapeutical compounds containing them | |
KR940005279A (en) | Pharmaceutical Compositions Containing Amidine and Amidine | |
GB8608893D0 (en) | D-nor-7-ergoline derivatives | |
IE780920L (en) | Substituted diaminopropane compositions | |
ES2061579T3 (en) | CEFEM COMPOUNDS AND PROCEDURES FOR ITS PREPARATION. |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AU DK FI JP KR NO US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE FR GB IT LU NL SE |