WO2003024454A2 - Topical composition containing brucine and the use for the treatment of damaged mammalian skin - Google Patents

Topical composition containing brucine and the use for the treatment of damaged mammalian skin Download PDF

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Publication number
WO2003024454A2
WO2003024454A2 PCT/EP2002/010522 EP0210522W WO03024454A2 WO 2003024454 A2 WO2003024454 A2 WO 2003024454A2 EP 0210522 W EP0210522 W EP 0210522W WO 03024454 A2 WO03024454 A2 WO 03024454A2
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Prior art keywords
brucine
approximately
composition according
oil
composition
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Ceased
Application number
PCT/EP2002/010522
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French (fr)
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WO2003024454A3 (en
Inventor
Anthony Vila
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Tig Investments Ltd
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Tig Investments Ltd
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Filing date
Publication date
Application filed by Tig Investments Ltd filed Critical Tig Investments Ltd
Priority to US10/490,065 priority Critical patent/US20040248930A1/en
Priority to AU2002342718A priority patent/AU2002342718B2/en
Priority to NZ532332A priority patent/NZ532332A/en
Priority to EP02779378A priority patent/EP1434582B1/en
Priority to DE60203726T priority patent/DE60203726T2/en
Priority to AT02779378T priority patent/ATE292970T1/en
Publication of WO2003024454A2 publication Critical patent/WO2003024454A2/en
Publication of WO2003024454A3 publication Critical patent/WO2003024454A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite

Definitions

  • This invention relates to a topical composition.
  • a dermatological composition suitable for topical application to mammalian skin.
  • Such composition is useful in the cosmetic or medical treatment of damaged mammalian skin, especially damage caused by sunburn, minor burns, ulcers or the like.
  • Brucine (2 , 3-dimethoxystrychnidin-10-one) is a highly toxic alkaloid resembling strychnine, which can be used as an addition agent for lubricants .
  • brucine or a dermatologically acceptable derivative thereof is useful in the regeneration of mammalian tissue.
  • brucine or a dermatologically acceptable salt thereof, or a hydrate thereof, in the manufacture of a medicament for the treatment of damaged mammalian skin.
  • the invention also provides a dermatological composition suitable for topical application to mammalian skin, which comprises:
  • the balance comprising a dermatologically acceptable oil or water or a combination thereof.
  • brucine is preferably used in the form of a salt, more preferably its sulphate salt.
  • brucine is used in the form of brucine sulphate heptahydrate.
  • Brucine or a salt thereof or a hydrate thereof is preferably present in the composition in an amount of from approximately 0.1-0.2%, especially approximately 0.15%, by weight of the composition.
  • the hydroxy acid used in the composition of the present invention may be any suitable hydroxy acid, such as, for example, glycolic, lactic, malic, tartaric, citric, mandelic or salicylic acid or a mixture thereof.
  • the hydroxy acid may be present in the form of the free acid and/or in the form of one of its associated salts, especially salts with an organic base or an alkali metal, or in the form of an ester or amide thereof.
  • Sodium salicylate is particularly preferred.
  • the hydroxy acid is preferably present in the composition in an amount of from approximately 1.0-2.5%, more preferably approximately 1.2-1.8%, and especially approximately 1.5%, by weight of the composition.
  • Component (c) of the composition comprises water in an amount of from approximately 0.15-5%, preferably from approximately 0.5-3%, more preferably from approximately 0.75-2.5%, and especially approximately 2%, by weight of the composition.
  • Component (d) of the composition comprises a dermatologically acceptable oil, or water, or a combination thereof.
  • the composition is in the form of a water-in-oil emulsion.
  • component (d) consists of a dermatologically acceptable oil. Any suitable oil may be used, such as mineral oil or a vegetable oil, e.g. sunflower oil, or a mixture thereof. Pure mineral oil is preferred. In a particularly preferred embodiment, the mineral oil is free from preservative.
  • component (d) of the composition consists of water.
  • composition of the invention may also include a masking agent such as caffeine or the like, preferably in an amount of from approximately 0.03-0.08%, especially approximately 0.05%, by weight of the composition.
  • a masking agent such as caffeine or the like, preferably in an amount of from approximately 0.03-0.08%, especially approximately 0.05%, by weight of the composition.
  • the composition of the invention may be formed by (a) heating the brucine or salt thereof or hydrate thereof in a suitable solvent, such as an alcohol, preferably ethanol or isopropanol, until the brucine is dissolved; (b) adding the hydroxy acid and masking agent (if used) to the water or a portion thereof and heating to a temperature in the range of from 70°C to 85°C until they are dissolved; (c) heating the oil, if present, to a temperature in the range of from 70°C to 85°C; (d) mixing the brucine and hydroxy acid solutions and any of the water remaining, or, if oil is present, adding the brucine and hydroxy acid solutions and any of the water remaining, to the heated oil; and (e) heating the resulting product to a temperature in the range of from 80°C to 95°C so as to evaporate substantially all of the solvent. The resulting product may then be homogenised until fully blended.
  • a suitable solvent such as an alcohol, preferably ethanol or isopropanol
  • a water-in-oil emulsion was prepared by adding the sodium salicylate and caffeine to the water and heating to approximately 80°C for 1-2 minutes until clear.
  • the brucine sulphate heptahydrate was dissolved in approximately 20.0 ml of ethanol by heating to a temperature of approximately 80°C.
  • the mineral oil was heated to approximately 80°C and the sodium salicylate/caffeine and brucine solutions were added thereto.
  • the resulting product was heated to approximately 90°C for approximately 5 - 10 minutes to evaporate the ethanol .
  • the product was then homogenised until fully blended.
  • An aqueous formulation was prepared by adding the sodium salicylate and caffeine to the water and heating to approximately 80°C for 1-2 minutes until clear.
  • the brucine sulphate heptahydrate was dissolved in approximately 20.0 ml of ethanol by heating to a temperature of approximately 80°C.
  • the sodium salicylate/caffeine and brucine solutions were mixed together and heated to approximately 90°C for approximately 5 - 10 minutes to evaporate the ethanol.
  • the compositions prepared in Examples 1 and 2 were found to be effective in reducing trauma and regenerating damaged skin resulting from sunburn, minor burns and ulcers .
  • Severity of burn indicates a standard used by those 5 involved in this clinical study to identify the severity of a burn, 1 being least painful and 5 being most painful.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

This invention concerns the use of the brucine (2,3-dimethoxystrychnidin-10-one) or a dermatologically acceptable derivative thereof in the treatment of damaged mammalian skin.

Description

TOPICAL COMPOSITION
This invention relates to a topical composition. In particular, it relates to a dermatological composition suitable for topical application to mammalian skin. Such composition is useful in the cosmetic or medical treatment of damaged mammalian skin, especially damage caused by sunburn, minor burns, ulcers or the like.
Brucine (2 , 3-dimethoxystrychnidin-10-one) is a highly toxic alkaloid resembling strychnine, which can be used as an addition agent for lubricants .
It has now unexpectedly been found that brucine or a dermatologically acceptable derivative thereof is useful in the regeneration of mammalian tissue.
According to the present invention there is provided the use of brucine or a dermatologically acceptable salt thereof, or a hydrate thereof, in the manufacture of a medicament for the treatment of damaged mammalian skin.
The invention also provides a dermatological composition suitable for topical application to mammalian skin, which comprises:
(a) approximately 0.05-0.3% by weight of brucine or a dermatologically acceptable salt thereof, or a hydrate thereof; (b) approximately 0.8-3% by weight of a hydroxy acid or a salt, ester or amide thereof;
(c) approximately 0.15-5% by weight of water; and
(d) the balance comprising a dermatologically acceptable oil or water or a combination thereof.
In the present invention, brucine is preferably used in the form of a salt, more preferably its sulphate salt. In a particularly preferred embodiment, brucine is used in the form of brucine sulphate heptahydrate. Brucine or a salt thereof or a hydrate thereof is preferably present in the composition in an amount of from approximately 0.1-0.2%, especially approximately 0.15%, by weight of the composition.
The hydroxy acid used in the composition of the present invention may be any suitable hydroxy acid, such as, for example, glycolic, lactic, malic, tartaric, citric, mandelic or salicylic acid or a mixture thereof. The hydroxy acid may be present in the form of the free acid and/or in the form of one of its associated salts, especially salts with an organic base or an alkali metal, or in the form of an ester or amide thereof. Sodium salicylate is particularly preferred. The hydroxy acid is preferably present in the composition in an amount of from approximately 1.0-2.5%, more preferably approximately 1.2-1.8%, and especially approximately 1.5%, by weight of the composition. Component (c) of the composition comprises water in an amount of from approximately 0.15-5%, preferably from approximately 0.5-3%, more preferably from approximately 0.75-2.5%, and especially approximately 2%, by weight of the composition.
Component (d) of the composition comprises a dermatologically acceptable oil, or water, or a combination thereof. In a preferred embodiment, the composition is in the form of a water-in-oil emulsion. In a particularly preferred embodiment, component (d) consists of a dermatologically acceptable oil. Any suitable oil may be used, such as mineral oil or a vegetable oil, e.g. sunflower oil, or a mixture thereof. Pure mineral oil is preferred. In a particularly preferred embodiment, the mineral oil is free from preservative.
In a further preferred embodiment, component (d) of the composition consists of water.
The composition of the invention may also include a masking agent such as caffeine or the like, preferably in an amount of from approximately 0.03-0.08%, especially approximately 0.05%, by weight of the composition.
The composition of the invention may be formed by (a) heating the brucine or salt thereof or hydrate thereof in a suitable solvent, such as an alcohol, preferably ethanol or isopropanol, until the brucine is dissolved; (b) adding the hydroxy acid and masking agent (if used) to the water or a portion thereof and heating to a temperature in the range of from 70°C to 85°C until they are dissolved; (c) heating the oil, if present, to a temperature in the range of from 70°C to 85°C; (d) mixing the brucine and hydroxy acid solutions and any of the water remaining, or, if oil is present, adding the brucine and hydroxy acid solutions and any of the water remaining, to the heated oil; and (e) heating the resulting product to a temperature in the range of from 80°C to 95°C so as to evaporate substantially all of the solvent. The resulting product may then be homogenised until fully blended.
The invention will be more clearly understood from the following description thereof given by way of example only.
EXAMPLE 1
Figure imgf000005_0001
A water-in-oil emulsion was prepared by adding the sodium salicylate and caffeine to the water and heating to approximately 80°C for 1-2 minutes until clear. The brucine sulphate heptahydrate was dissolved in approximately 20.0 ml of ethanol by heating to a temperature of approximately 80°C. The mineral oil was heated to approximately 80°C and the sodium salicylate/caffeine and brucine solutions were added thereto. The resulting product was heated to approximately 90°C for approximately 5 - 10 minutes to evaporate the ethanol . The product was then homogenised until fully blended.
EXAMPLE 2
Figure imgf000006_0001
An aqueous formulation was prepared by adding the sodium salicylate and caffeine to the water and heating to approximately 80°C for 1-2 minutes until clear. The brucine sulphate heptahydrate was dissolved in approximately 20.0 ml of ethanol by heating to a temperature of approximately 80°C. The sodium salicylate/caffeine and brucine solutions were mixed together and heated to approximately 90°C for approximately 5 - 10 minutes to evaporate the ethanol. The compositions prepared in Examples 1 and 2 were found to be effective in reducing trauma and regenerating damaged skin resulting from sunburn, minor burns and ulcers .
The results of a clinical study carried out using the emulsion of Example 1 are shown in Table I.
TABLE I
Figure imgf000008_0001
Table I (cont ' d)
Figure imgf000009_0001
• Severity of burn indicates a standard used by those 5 involved in this clinical study to identify the severity of a burn, 1 being least painful and 5 being most painful.
• The amount of formulation applied was sufficient to 10 cover the area being treated. • Patient No. 8 had previously been to three other doctors and had not found success with any treatment until she had used the product of Example 1. She had not been to work for three days .
• Patients in this clinical study were all able to return to work or school with no problems after using the product of Example 1.
The invention is not limited to the embodiments and examples described herein which may be modified or varied without departing from the scope of the invention.

Claims

CLAIMS :
1. The use of brucine (2,3- dimethoxystrychnidin-10-one) or a dermatologically acceptable salt thereof, or a hydrate thereof, in the manufacture of a medicament for the treatment of damaged mammalian skin.
2. Use according to claim 1 wherein brucine is in the form of brucine sulphate heptahydrate.
3. A dermatological composition suitable for topical application to mammalian skin, which comprises:
(a) approximately 0.05-0.3% by weight of brucine or a dermatologically acceptable salt thereof, or a hydrate thereof;
(b) approximately 0.8-3% by weight of a hydroxy acid or a salt, ester or amide thereof;
(c) approximately 0.15-5% by weight of water; and
(d) the balance comprising a dermatologically acceptable oil or water or a combination thereof.
4. A composition according to claim 3, wherein brucine is in the form of brucine sulphate heptahydrate.
5. A composition according to claim 3 or 4, wherein brucine or a salt thereof or a hydrate thereof is present in an amount of from approximately 0.1-0.2%, especially approximately 0.15% by weight of the composition.
6. A composition according to one or more of claims 3 to 5 , wherein the hydroxy acid is selected from glycolic, lactic, malic, tartaric, citric, mandelic or salicylic acid, or a salt thereof, or a mixture thereof, preferably sodium salicylate.
7. A composition according to one or more of claims 3 to 6, wherein the hydroxy acid or salt, ester or amide thereof is present in an amount of from approximately 1.0-2.5%, preferably approximately 1.2-1.8%, and especially approximately 1.5%, by weight of the composition.
8. A composition according to one or more of claims 3 to 7 , wherein component (c) of the composition comprises water in an amount of from approximately 0.5-3%, preferably from approximately 0.75-2.5%, and especially approximately 2%, by weight of the composition.
9. A composition according to one or more of claims 3 to 8, wherein component (d) consists of water.
10. A composition according to one or more of claims 3 to 8 , which is in the form of a water-in-oil emulsion, wherein preferably, component (d) consists of a dermatologically acceptable oil.
11. A composition according to one or more of claims 3 to 8 or 10, wherein the dermatologically acceptable oil is mineral oil or a vegetable oil, or a mixture thereof.
12. A composition according to claim 11, wherein the oil is mineral oil, preferably mineral oil which is free from preservative.
13. A composition according to one or more of the preceding claims, further comprising a masking agent, preferably caffeine, the masking agent preferably being present in an amount of from approximately 0.03-0.08%, especially approximately 0.05%, by weight of the composition.
14. A composition according to one or more of claims 3 to 13 for use in the treatment of damaged mammalian skin.
15. A method of preparing a composition according to one or more of claims 3 to 13 , comprising the following steps:
(a) heating the brucine or salt thereof or hydrate thereof in a solvent, preferably ethanol, until the brucine is dissolved; (b) adding the hydroxy acid and masking agent, if present, to the water or a portion thereof and heating to a temperature in the range of from 70°C to 85°C until they are dissolved; (c) heating the oil, if present, to a temperature in the range of from 70°C to 85°C;
(d) mixing the brucine and hydroxy acid solutions and any of the water remaining, or, if oil is present, adding the brucine and hydroxy acid solutions and any of the water remaining, to the heated oil; and
(e) heating the resulting product to a temperature in the range of from 80°C to 95°C so as to evaporate substantially all of the solvent.
PCT/EP2002/010522 2001-09-20 2002-09-18 Topical composition containing brucine and the use for the treatment of damaged mammalian skin Ceased WO2003024454A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US10/490,065 US20040248930A1 (en) 2001-09-20 2002-09-18 Topical composition
AU2002342718A AU2002342718B2 (en) 2001-09-20 2002-09-18 Topical composition containing brucine and the use for the treatment of damaged mammalian skin
NZ532332A NZ532332A (en) 2001-09-20 2002-09-18 Composition comprising brucine (2,3-dimethoxystrychindin-10-one) to be applied topically to treat damaged mamalian skin
EP02779378A EP1434582B1 (en) 2001-09-20 2002-09-18 Topical composition containing brucine and the use for the treatment of damaged mammalian skin
DE60203726T DE60203726T2 (en) 2001-09-20 2002-09-18 TOPICAL COMPOSITION CONTAINING BRUCIN AND ITS USE FOR THE TREATMENT OF SKIN DAMAGE
AT02779378T ATE292970T1 (en) 2001-09-20 2002-09-18 TOPICAL COMPOSITION CONTAINING BRUCIN AND USE THEREOF FOR TREATING SKIN DAMAGE

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IES010841 2001-09-20
IE20010841 2001-09-20

Publications (2)

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WO2003024454A2 true WO2003024454A2 (en) 2003-03-27
WO2003024454A3 WO2003024454A3 (en) 2003-08-28

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PCT/EP2002/010522 Ceased WO2003024454A2 (en) 2001-09-20 2002-09-18 Topical composition containing brucine and the use for the treatment of damaged mammalian skin

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US (1) US20040248930A1 (en)
EP (1) EP1434582B1 (en)
CN (1) CN1304004C (en)
AT (1) ATE292970T1 (en)
AU (1) AU2002342718B2 (en)
DE (1) DE60203726T2 (en)
ES (1) ES2242075T3 (en)
NZ (1) NZ532332A (en)
WO (1) WO2003024454A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1461021A4 (en) * 2001-12-05 2009-10-21 Xitian Zhang Transdermal drug delivery system of strychnine, brucine, securinine and their salts

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101972259B (en) * 2010-06-08 2012-04-25 北京大学 Brucine and application of derivatives thereof in preparation of drugs for treating alcoholic abuse and dependence

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531570A (en) * 1967-04-03 1970-09-29 American Home Prod Method of tranquilizing or anti-depressant treatment with alkaloid derivatives
US5378461A (en) * 1991-07-12 1995-01-03 Neigut; Stanley J. Composition for the topical treatment of skin damage
JP3623548B2 (en) * 1995-06-01 2005-02-23 協和醗酵工業株式会社 Cosmetics
MY124445A (en) * 1995-10-12 2006-06-30 Ono Foods Ind Co Ltd Method of drying foods by using far infrared rays at reduced pressure and temperature
US5747021A (en) * 1997-01-10 1998-05-05 Mckenzie; Therman After shave treatment composition
CN100594027C (en) * 2001-12-05 2010-03-17 张喜田 Percutaneous medicine of strychnine, toxiferine, securinine and salt thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1461021A4 (en) * 2001-12-05 2009-10-21 Xitian Zhang Transdermal drug delivery system of strychnine, brucine, securinine and their salts

Also Published As

Publication number Publication date
WO2003024454A3 (en) 2003-08-28
NZ532332A (en) 2006-11-30
DE60203726D1 (en) 2005-05-19
ATE292970T1 (en) 2005-04-15
DE60203726T2 (en) 2006-02-09
ES2242075T3 (en) 2005-11-01
CN1304004C (en) 2007-03-14
EP1434582A2 (en) 2004-07-07
EP1434582B1 (en) 2005-04-13
US20040248930A1 (en) 2004-12-09
CN1556704A (en) 2004-12-22
AU2002342718B2 (en) 2007-10-18

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