CH667651A5 - SALTS OF 5-OXOPROLIN AND 6-PIPERIDINO-2,4-DIAMINOPYRIMIDIN-3-OXIDE AND USE. - Google Patents
SALTS OF 5-OXOPROLIN AND 6-PIPERIDINO-2,4-DIAMINOPYRIMIDIN-3-OXIDE AND USE. Download PDFInfo
- Publication number
- CH667651A5 CH667651A5 CH2045/86A CH204586A CH667651A5 CH 667651 A5 CH667651 A5 CH 667651A5 CH 2045/86 A CH2045/86 A CH 2045/86A CH 204586 A CH204586 A CH 204586A CH 667651 A5 CH667651 A5 CH 667651A5
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- CH
- Switzerland
- Prior art keywords
- formula
- salt
- water
- piperidino
- oxide
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- 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
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- 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
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
BESCHREIBUNG Diese Beschreibung betrifft das Salz, gebildet aus 5-Oxoprolin und 6-Piperidino-2,4-diaminopyrimidin-3-oxid gemäss Formel (I) DESCRIPTION This description relates to the salt formed from 5-oxoproline and 6-piperidino-2,4-diaminopyrimidine-3-oxide according to formula (I)
NH2 NH2
Das erfindungsgemässe Salz der Formel 1, seine Herstellung und seine Verwendung sind in den Patentansprüchen charakterisiert. The salt of formula 1 according to the invention, its preparation and its use are characterized in the claims.
Die Verbindung der Formel (I) zeigt Aktivitäten hinsichtlich der Beschleunigung und der Verbesserung des Haarwuchses bei Menschen und bei Tieren. Entsprechende Zusammensetzungen können daher sowohl auf dem Gebiet der Kosmetik wie auch auf demjenigen der Pharmazie oder auch in der Veterinärmedizin verwendet werden. Die Anwendung geschieht dabei immer in topischer Form. The compound of formula (I) shows activities in accelerating and improving hair growth in humans and animals. Appropriate compositions can therefore be used both in the field of cosmetics and in the field of pharmacy or also in veterinary medicine. The application is always topical.
Das Derivat des 2,4-Diaminopyrimidins, welches die basische Komponente der Verbindung der Formel (I) darstellt, ist unter dem internazionalen Handelsnamen «Minoxidil» bekannt. Die Verbindung wird angewendet in der Humanmedizin zur Behandlung von Hypertensivität aber auch für die topische Behandlung von Kahlheit und Alopezie, speziell Alopecia areata. The derivative of 2,4-diaminopyrimidine, which is the basic component of the compound of formula (I), is known under the international trade name "Minoxidil". The compound is used in human medicine for the treatment of hypertension but also for the topical treatment of baldness and alopecia, especially alopecia areata.
Wegen der Unlöslichkeit von Minoxidil in Wasser sind seine flüssigen Formulierungen aufgebaut auf Gykolen und Polyalkoholen. Derartige Zusammensetzungen sind aber bekannterweise unangenehm für die topische Anwendung; sie führen zu einem öligen Aussehen der Kopfhaut. Because of the insolubility of minoxidil in water, its liquid formulations are based on glycols and polyalcohols. Such compositions are known to be unpleasant for topical use; they give the scalp an oily appearance.
Das erfindungsgemässe Salz ist dagegen gut wasserlöslich und kann daher leicht in auf Wasser basierenden Formulierungen angewendet werden. In contrast, the salt according to the invention is readily water-soluble and can therefore be easily used in water-based formulations.
Die saure Komponente des Salzes der Formel (I) das L-5-Oxoprolin, auch bekannt als Pyroglutaminsäure (PGA) wird ebenfalls schon im kosmetisch/dermatologischen Gebiet verwendet und zwar als Feuchthaltefaktor. Die Verbindung wirkt in dem Sinne, dass sie optimale Bedingungen für die Befeuchtung von Haar und Kopfhaut schafft. Sie verhindert deswegen auch pathologische Veränderungen derselben. The acidic component of the salt of formula (I), L-5-oxoproline, also known as pyroglutamic acid (PGA), is also already used in the cosmetic / dermatological field, specifically as a moisturizing factor. The compound works in the sense that it creates optimal conditions for moisturizing the hair and scalp. It therefore prevents pathological changes in the same.
Es wurde nun festgestellt, dass das neue Salz der Formel (I), welches Gegenstand dieser Erfindung ist und im folgenden unter der Kurzbezeichnung MT/1 aufgeführt werden wird, ausgezeichnete Eigenschaften und Aktivitäten hinsichtlich der Verhinderung und Behandlung von Haarausfall zeigt. It has now been found that the new salt of formula (I), which is the subject of this invention and will be listed below under the short name MT / 1, exhibits excellent properties and activities with regard to the prevention and treatment of hair loss.
Diese günstigen Eigenschaften zeigen sich hinsichtlich aller Haare beim Menschen. These favorable properties are evident with regard to all hair in humans.
Die neue Verbindung zeigt sich in der genannten Anwendung auch überlegen in Vergleichsexperimenten mit Minoxidil allein. Es hat sich nämlich gezeigt, dass MT/1 leichter absorbiert wird als Minoxidil allein. In the application mentioned, the new compound is also superior in comparison experiments with minoxidil alone. It has been shown that MT / 1 is more easily absorbed than minoxidil alone.
Das erfindungsgemässe Salz der Formel (I) ist, wie oben schon gesagt, wasserlöslich und diese Eigenschaft führt dazu, dass es gut in Zusammenstzungen verwendet werden kann, deren Basis reines Wasser oder doch zur Hauptsache Wasser ist. Derartige Zusammensetzungen sind z.B. sehr wichtig für die Behandlung von Trichonodose, d.h. dem spontanen Auftreten von Knoten und Schlingen im Haar. The salt of the formula (I) according to the invention is, as already mentioned above, water-soluble and this property means that it can be used well in compositions whose basis is pure water or, at the very least, water. Such compositions are e.g. very important for the treatment of trichonodosis, i.e. the spontaneous appearance of knots and loops in the hair.
Sowohl die systemische Toxizität wie auch die Toleranz auf der Haut von MT/1 liegen eindeutig innerhalb der bekannten Werte für Minoxidil allein, wenn dieses topisch angewendet wird. Both the systemic toxicity and the tolerance on the skin of MT / 1 are clearly within the known values for minoxidil alone when applied topically.
Daher kann die Verbindung der Formel (I) leicht und mit Vorteil in folgenden Formulierungen verwendet werden: Lotionen, Salben, Sprays, Schampoos, Gelen, Brillantinen und Haarfixiermitteln, alle möglichst auf reiner Wasserbasis oder doch auf Basis von vor allem Wasser. Die genannten Formulierungen können, neben der Verbindung der Formel (I), die bekannten andern aktiven und passiven Komponenten enthalten, wie die üblichen, geeigneten Träger- und Zusatzstoffe, Geruchsstoffe, Stabilisatoren, Farbmittel usw. Therefore, the compound of formula (I) can be easily and advantageously used in the following formulations: lotions, ointments, sprays, shampoos, gels, brilliants and hair fixatives, all preferably on a pure water basis or based on water. In addition to the compound of the formula (I), the formulations mentioned can contain the known other active and passive components, such as the customary, suitable carriers and additives, odorants, stabilizers, colorants, etc.
Die genannten Formulierungen können den Wirkstoff in einem Gehalt von 0,1 bis 10 Gew.-% enthalten; sie werden üblicherweise ein- bis zweimal täglich auf die zu behandelnde Hautstelle aufgetragen. The formulations mentioned can contain the active ingredient in a content of 0.1 to 10% by weight; they are usually applied to the area of skin to be treated once or twice a day.
Die Herstellung der Verbindung der Formel (I) kann auch in geeigneten Lösungsmitteln ausgeführt werden, wie z.B. in Methanol, Äthanol, Isopropanol usw., und zwar sowohl in wasserfreier wie in teilweise hydrierter Form. The preparation of the compound of formula (I) can also be carried out in suitable solvents such as e.g. in methanol, ethanol, isopropanol, etc., both in anhydrous and in partially hydrogenated form.
Die Verbindung der Formel (I) wird schliesslich isoüert und zwar mittels konventioneller Methoden wie Abdampfen der Lösungsmittel, Ausfällen mit Flüssigkeiten, in denen die Verbindung nicht löslich ist usw. The compound of formula (I) is finally isolated using conventional methods such as evaporation of the solvent, precipitation with liquids in which the compound is not soluble, etc.
Die folgenden Beispiele illustrieren die Erfindung, ohne sie in irgend einer Form einzuschränken: The following examples illustrate the invention without restricting it in any way:
Beispiel 1 example 1
Zu einer Suspension von 2 g Minoxidil in 50 ml Wasser werden 1,3 g L-Oxoprolin gegeben. 1.3 g of L-oxoproline are added to a suspension of 2 g of minoxidil in 50 ml of water.
Die dabei erhaltene Lösung kann entweder als solche für die Herstellung von erfindungsgemässen Zusammensetzungen für die topische Anwendung verwendet werden oder die Verbindung der Formel (I) kann daraus in fester Form isoliert werden. Dies kann z.B. mittels Verdampfen des Wassers bei tiefem Druck geschehen. Die dabei erhaltene chemische Verbindung ist, wie die Analyse mittels IR zeigt, chemisch rein. The solution obtained in this way can either be used as such for the preparation of compositions according to the invention for topical use, or the compound of the formula (I) can be isolated therefrom in solid form. This can e.g. done by evaporating the water at low pressure. The chemical compound obtained is, as analysis by IR shows, chemically pure.
Beispiel 2 Example 2
2,09 g Minoxidil und 1,29 g L-Oxoprolin werden in 2.09 g minoxidil and 1.29 g L-oxoproline are in
2 2nd
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
667 651 667 651
100 ml 95%igem Äthanol gelöst. Die so erhaltene Lösung kann als solche, gegebenenfalls weiter verdünnt oder mit andern Stoffen versetzt, verwendet werden. Die Verbindung der Formel (I) kann aber auch daraus isoliert werden, und zwar entweder durch totale Verdampfung des Lösungsmittels oder teilweise Verdampfung und Versetzen der Restlösung mit Äthyläther als Insolubilisierungsmittel. 100 ml of 95% ethanol dissolved. The solution thus obtained can be used as such, optionally further diluted or mixed with other substances. The compound of formula (I) can also be isolated therefrom, either by total evaporation of the solvent or partial evaporation and adding ethyl ether as the insolubilizing agent to the residual solution.
Der erhaltene Feststoff entspricht chemisch der Formel The solid obtained chemically corresponds to the formula
(I). (I).
Beispiel 3 Example 3
In diesem Beispiel werden verschiedene Formulierungsmöglichkeiten angegeben. Die darin verwendeten Salze der Formel (I) (MT/1) sind diejenigen, die in den Beispielen 1 und 2 erhalten wurden. In this example, various formulation options are given. The salts of formula (I) (MT / 1) used therein are those obtained in Examples 1 and 2.
a) Lotion MT/1 a) Lotion MT / 1
Natriumascorbat Konservierungsmittel parfümiertes und gefärbtes Wasser b) Lotion MT/1 Vitamin H Inosit (R) Sodium ascorbate preservative, perfumed and colored water b) Lotion MT / 1 Vitamin H Inosit (R)
Calciumpanthotenat Aminosäurekomplex Vitamin-B-Komplex Isopropylalkohol parfümiertes Wasser c) Lotion MT/1 Calcium panthotenate amino acid complex Vitamin B complex isopropyl alcohol perfumed water c) Lotion MT / 1
Ucon (R) 75-H-450 Vancide (R) 89RE Riechstoff Ucon (R) 75-H-450 Vancide (R) 89RE fragrance
Äthylalkohol 95 Grad Wasser d) Aerosol-Lotion MT/1 Panthenol Lanogel 21 (R) Ethyl alcohol 95 degrees water d) Aerosol lotion MT / 1 Panthenol Lanogel 21 (R)
Zelek MK (R) (Antistati-kum) Zelek MK (R) (anti-static)
Riechstoff Alkohol Fragrance alcohol
Freon (R) 11/12 (60:40) Freon (R) 11/12 (60:40)
e) Lotion MT/1 Alkohol Riechstoff Farbstoff Wasser f) Lotion MT/1 Resorcin e) Lotion MT / 1 alcohol fragrance dye water f) Lotion MT / 1 resorcinol
Capsicum-Tinktur Capsicum tincture
3,38 g 0,5 g q.s. 3.38 g 0.5 g q.s.
q.s. auf 100 g q.s. to 100 g
3,38 g 3.38 g
1 g 1 g
1 g 1 g
2 g 0,2 g 5 g 2 g 0.2 g 5 g
520 s q.s. auf 1000 g 520 s q.s. to 1000 g
3,38 g 10 g 0,1 g q.s. 3.38 g 10 g 0.1 g q.s.
50 g q.s. auf 100 g 50 g q.s. to 100 g
3,38 g 3.38 g
1 g 1 g
0,5 g 0.5 g
0,1 g q.s. 0.1 g q.s.
25 g 25 g
70 e 70 e
3,38 g 30 g Spuren q.s. 3.38 g 30 g traces q.s.
q.s. auf 100 g q.s. to 100 g
3,38 g 5 g 5 g 3.38 g 5 g 5 g
Ricinusöl Alkohol 90 Grad Riechstoff Castor oil alcohol 90 degrees fragrance
5 g) Lotion MT/1 5 g) lotion MT / 1
Betanaphthol Glycerin Betanaphthol glycerin
Alkohol 90 Grad 10 Riechstoff Wasser h) Lotion MT/1 15 Isopropylalkohol Riechstoff Salizylsäure Wasser Alcohol 90 degrees 10 fragrance water h) Lotion MT / 1 15 isopropyl alcohol fragrance salicylic acid water
20 i) Aerosol-Schaum-Lotion MT/1 20 i) Aerosol foam lotion MT / 1
Cetylalkohol SapogenatT/100 (R) Neo-Extrapon H (R) 25 Iso-Adipat (R) Cetyl alcohol SapogenatT / 100 (R) Neo-Extrapon H (R) 25 Iso-Adipat (R)
Neo-PCL, wasserlöslich Menthol Neo-PCL, water soluble menthol
Emuisogen OG (R) Hostaphat KL/340 (R) 30 Äthylalkohol Riechstoff Wasser Emuisogen OG (R) Hostaphat KL / 340 (R) 30 ethyl alcohol fragrance water
Formulierung 35 Treibstoff: 12/114(10:60) Formulation 35 Fuel: 12/114 (10:60)
l) Crème m) Schampoo so MT/1 l) creme m) shampoo so MT / 1
Saccharose-Monolaurat Riechstoff und Farbe Wasser Sucrose monolaurate fragrance and color water
55 n) Haarfestiger MT/1 55 n) Hair set MT / 1
Natriumalginat Calciumcitrat Alkohol 60 Riechstoff Sodium alginate calcium citrate alcohol 60 fragrance
Konservierungsmittel Wasser Preservative water
5 g q.s. auf 100 g q.s. 5 g q.s. to 100 g q.s.
3,38 g 0,5 g 5 g 50 g q.s. 3.38 g 0.5 g 5 g 50 g q.s.
q.s. auf 100 j q.s. to 100 y
3,38 g 50 g q.s. 3.38 g 50 g q.s.
0,2 g q.s. auf 100 g 0.2 g q.s. to 100 g
3,38 g 3.38 g
0,8 0.8
g G
0,2 0.2
g G
2 2nd
g G
1 1
g G
2 2nd
g G
0,2 0.2
g G
2 2nd
g G
2,5 2.5
g G
45 45
g G
1,2 1.2
g q.s. auf 100 g g q.s. to 100 g
85 g 15 g 85 g 15 g
MT/1 MT / 1
3,38 3.38
g G
Diglycolstearat Diglycol stearate
12 12
g G
40 Triäthanolaminstearat 40 triethanolamine stearate
5 5
g G
Lanolin lanolin
4 4th
g G
Cholesterin cholesterol
5 5
g G
Lecithin Lecithin
0,5 0.5
g G
Diäthylsebacat Diethyl sebacate
0,5 0.5
g G
45 Isopropylmyristat 45 isopropyl myristate
10 10th
g G
Konservierungsmittel q.s. Preservatives q.s.
Wasser water
63 63
g G
3,38 g 50 g q.s. 3.38 g 50 g q.s.
q.s. auf 100 g q.s. to 100 g
3,84 g 1,2 g 0,1 g 3.84 g 1.2 g 0.1 g
3 g q.s. 3 g q.s.
q.s. q.s.
q.s. auf 100 g q.s. to 100 g
C C.
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8520836A IT1214610B (en) | 1985-05-22 | 1985-05-22 | COMPOUND FOR DERMATOLOGICAL COSMETIC USE AND RELATED COMPOSITIONS. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH667651A5 true CH667651A5 (en) | 1988-10-31 |
Family
ID=11172771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2045/86A CH667651A5 (en) | 1985-05-22 | 1986-05-21 | SALTS OF 5-OXOPROLIN AND 6-PIPERIDINO-2,4-DIAMINOPYRIMIDIN-3-OXIDE AND USE. |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPH0651616B2 (en) |
| CH (1) | CH667651A5 (en) |
| DE (1) | DE3617124A1 (en) |
| FR (1) | FR2582304B1 (en) |
| GB (1) | GB2175901B (en) |
| IL (2) | IL78842A0 (en) |
| IT (1) | IT1214610B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2636840B1 (en) * | 1988-09-23 | 1990-12-21 | Norchim Sarl | SALT OF 6-PIPERIDINO-2,4-DIAMINOPYRIMIDINE-3-OXIDE AND ACETURIC ACID, THEIR PREPARATION AND THEIR DERMATOCOSMETOLOGICAL APPLICATIONS |
| US5300510A (en) * | 1988-09-23 | 1994-04-05 | Norchim | Salt of 6-piperidino-2,4-diaminopyrimidine 3-oxide and aceturic acid, its preparation and its dermato-cosmetological application |
| FR2706896B1 (en) * | 1993-06-23 | 1996-04-12 | Caillot Jean Luc |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2188599A5 (en) * | 1972-06-12 | 1974-01-18 | Fabre Sa Pierre | (Pyro)glutamic acid derivs - from (substd) ethylenediamine, substd guanidine and dimethyl amino ethanol |
| LU73680A1 (en) * | 1975-10-29 | 1977-05-31 | ||
| US4139619A (en) * | 1976-05-24 | 1979-02-13 | The Upjohn Company | 6-Amino-4-(substituted amino)-1,2-dihydro-1-hydroxy-2-iminopyrimidine, topical compositions and process for hair growth |
| GB2140257B (en) * | 1980-12-04 | 1985-09-18 | Quantel Ltd | Video image creation |
| DE3280344D1 (en) * | 1981-11-09 | 1991-07-25 | Gail S Bazzano | USE OF RETINOIDES AND MINOXIDIL (2,4-DIAMINO-6-PIPERIDINO-PYRIMIDINE-3-OXIDE) TO IMPROVE THE GROWTH OF HUMAN HEAD HAIR AND TO TREAT CERTAIN TYPES OF ALOPECIA. |
| JPS5888306A (en) * | 1981-11-19 | 1983-05-26 | Takeo Kinji | Hair tonic cosmetic |
| JPS5888307A (en) * | 1981-11-19 | 1983-05-26 | Takeo Kinji | Minoxidil-containing hair tonic |
| US4452989A (en) * | 1982-06-01 | 1984-06-05 | Charles Of The Ritz Group Ltd. | Substantive moisturizing derivatives of 2-pyrrolidone-5-carboxylic acid and compositions containing same |
-
1985
- 1985-05-19 IL IL78842A patent/IL78842A0/en unknown
- 1985-05-22 IT IT8520836A patent/IT1214610B/en active Protection Beyond IP Right Term
-
1986
- 1986-05-19 IL IL78842A patent/IL78842A/en not_active IP Right Cessation
- 1986-05-21 CH CH2045/86A patent/CH667651A5/en not_active IP Right Cessation
- 1986-05-22 FR FR8607279A patent/FR2582304B1/en not_active Expired
- 1986-05-22 GB GB08612461A patent/GB2175901B/en not_active Expired
- 1986-05-22 JP JP61116286A patent/JPH0651616B2/en not_active Expired - Lifetime
- 1986-05-22 DE DE19863617124 patent/DE3617124A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT8520836A0 (en) | 1985-05-22 |
| GB2175901A (en) | 1986-12-10 |
| DE3617124A1 (en) | 1986-11-27 |
| JPH0651616B2 (en) | 1994-07-06 |
| JPS6269A (en) | 1987-01-06 |
| GB2175901B (en) | 1988-09-21 |
| FR2582304A1 (en) | 1986-11-28 |
| DE3617124C2 (en) | 1992-07-16 |
| FR2582304B1 (en) | 1989-06-02 |
| IL78842A (en) | 1989-09-28 |
| IL78842A0 (en) | 1986-09-30 |
| IT1214610B (en) | 1990-01-18 |
| GB8612461D0 (en) | 1986-07-02 |
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| Date | Code | Title | Description |
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| PUE | Assignment |
Owner name: WHITEHALL ITALIA S.P.A. |
|
| PL | Patent ceased |