WO2004002497A1 - Compositions contenant des glyco-alcaloides et leurs diverses utilisations - Google Patents

Compositions contenant des glyco-alcaloides et leurs diverses utilisations Download PDF

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Publication number
WO2004002497A1
WO2004002497A1 PCT/AU2003/000788 AU0300788W WO2004002497A1 WO 2004002497 A1 WO2004002497 A1 WO 2004002497A1 AU 0300788 W AU0300788 W AU 0300788W WO 2004002497 A1 WO2004002497 A1 WO 2004002497A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
glycoalkaloids
group
solasonine
solamargine
Prior art date
Application number
PCT/AU2003/000788
Other languages
English (en)
Inventor
Stephen John Carter
Elizabeth Williams
Original Assignee
Solbec Pharmaceuticals Limited
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.)
Filing date
Publication date
Application filed by Solbec Pharmaceuticals Limited filed Critical Solbec Pharmaceuticals Limited
Priority to CA002489675A priority Critical patent/CA2489675A1/fr
Priority to AU2003238544A priority patent/AU2003238544A1/en
Priority to NZ537267A priority patent/NZ537267A/en
Priority to EP03732115A priority patent/EP1539191A4/fr
Publication of WO2004002497A1 publication Critical patent/WO2004002497A1/fr

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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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/18—Feminine contraceptives
    • 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
    • A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention provides a composition comprising at least two glycoalkaloids of formula I:
  • either one or both of the dotted lines represents a double bond, and the other a single bond, or both represent single bonds;
  • the present invention also provides a pharmaceutical composition comprising a glycoalkaloid composition of the present invention and a pharmaceutically acceptable carrier.
  • the present invention also provides a method of treating cancer comprising the step of administering an effective amount of a composition or pharmaceutical composition of the present invention to a cancer patient.
  • the present invention also provides a method of terminating a pregnancy comprising the step of administering an effective amount of a composition or pharmaceutical composition of the present invention to a pregnant subject.
  • the present invention also provides a composition comprising about a 1 :1 ratio of solamargine and solasonine in isolated form.
  • Particularly preferred glycoalkaloids are solasodine glycosides such as solamargine and solasonine.
  • the present invention also provides a composition comprising solamargine and solasonine in a ratio between about 1 :6 and 6:1, 1 :4 and 4:1 , 1 :3 and 3:1 or 1 :2 to 2:1 on the proviso that the solasonine and solamargine do not constitute 66% of the glycosides in the composition.
  • the number of glycoalkaloids in the composition may be varied, as may their relative ratios in the composition. However, when the composition consists essentially of two glycoalkaloids they may be present in a ratio selected from the group of ratios consisting of: 1 :5; 1 :4; 1 :3; 1 :2 and 1 :1.
  • the mode of administration must, however, be at least suitable for the form in which the composition has been prepared.
  • the mode of administration for the most effective response may need to be determined empirically and the means of administration described below are given as examples and do not limit the method of delivery of the composition of the present invention in any way. All the formulations described below are commonly used in the pharmaceutical industry and are commonly known to suitably qualified practitioners.
  • the formulation will include the glycoalkaloid composition described as part of the invention and inert ingredients that allow for protection against the stomach environment and release of the glycoalkaloid in the intestine.
  • Targeted microparticles may be prepared by incorporating the Fab' fragment into the microparticles by a variety of techniques well known to those of skill in the art.
  • a biotin conjugated Fab' may be bound to a microparticle containing a streptavidin.
  • the biotinylated Fab' may be conjugated to a biotin derivatised microparticle by an avidin or streptavidin linker.
  • avidin or streptavidin linker typically about 30 to 125 and more typically about 50 to 100 Fab' fragments per microparticle/glycoalkaloid complex are used.
  • the pharmaceutical compositions of the present invention may also be formed into powders or some other form that is suitable for delivery by inhalation. Whilst inhalation may be via the mouth it will be appreciated that the route of delivery may also by via the nose.
  • the present invention also provides a method of treating psoriasis comprising the step of administering an effective amount of a composition or pharmaceutical composition of the present invention to a psoriasis patient.
  • the plurality of glycoalkaloids When the plurality of glycoalkaloids is administered as separate formulations they are preferably administered in a manner that mimics the delivery of a single formulation containing the glycoalkaloids. Thus, they may be administered simultaneously or in any other fashion that enables the glycoalkaloids to reach the target site simultaneously and achieve their therapeutic effect.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Endocrinology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Reproductive Health (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Pregnancy & Childbirth (AREA)
  • Molecular Biology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

L'inevntion concerne une composition comprenant au moins deux glyco-alcaloïdes de formule (I) dans laquelle : l'une des deux ou les deux lignes pointillées représente(nt) une liaison double et l'autre de ces deux lignes ou les deux lignes pointillées représente(nt) une liaison simple ; A représente un radical sélectionné parmi les radicaux de formules générales (II) et (V) ; chaque R1 représente un radical sélectionné séparément dans le groupe comprenant hydrogène, amino, oxo et OR4 ; chaque R2 représente un radical sélectionné séparément dans le groupe comprenant hydrogène, amino et OR4 ; chaque R3 représente un radical sélectionné séparément dans le groupe comprenant hydrogène, glucide et un dérivé glucidique ; « X » représente un radical sélectionné dans le groupe comprenant -CH2-, -0- et -NH2- ; ce composé comporte au moins un groupe R4 qui représente un glucide ou un dérivé glucidique sélectionné dans le groupe comprenant les substances glycéraldéhyde, érythrose, thréose, ribose, arabinose, xylose, lyxose, altrose, allose, gulose, mannose, glucose, idose, galactose, talose, rhamnose, dihydroxyactone, érythrulose, ribulose, xylulose, psicose, fructose, sorbose, tagatose, et autres hexoses, heptoses, octoses, nanoses, décoses, déoxysucres à chaînes ramifiées (par ex. apiose, hamamélose, streptose, cordycépose, mycarose et cladinose), des composés dont les groupes aldéhyde, cétone ou hydroxyle ont été substitués (par ex. N-acétyle, acétyle, méthyle, substitut de CH20H), alcools de sucre, acides de sucre, benzimidazoles, les sels énol des glucides, acides sacchariniques et phosphates de sucre ; la proportion desdits glyco-alcaloïdes est comprise entre 6:1 and 1:6 ; lorsque les glyco-alcaloïdes se présentent sous la forme de solamargine et de solasonine et sont présents selon une proportion égale à 1:1, les composés solamargine et solasonine doivent obligatoirement être isolés.
PCT/AU2003/000788 2002-07-01 2003-06-24 Compositions contenant des glyco-alcaloides et leurs diverses utilisations WO2004002497A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002489675A CA2489675A1 (fr) 2002-07-01 2003-06-24 Compositions contenant des glyco-alcaloides et leurs diverses utilisations
AU2003238544A AU2003238544A1 (en) 2002-07-01 2003-06-24 Glycoalkaloid compositions and various uses thereof.
NZ537267A NZ537267A (en) 2002-07-01 2003-06-24 Glycoalkaloid compositions and various uses thereof
EP03732115A EP1539191A4 (fr) 2002-07-01 2003-06-24 Compositions contenant des glyco-alcaloides et leurs diverses utilisations

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPS3290A AUPS329002A0 (en) 2002-07-01 2002-07-01 Glycoalkaloid compositions and various uses thereof
AUPS3290 2002-07-01

Publications (1)

Publication Number Publication Date
WO2004002497A1 true WO2004002497A1 (fr) 2004-01-08

Family

ID=3836847

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU2003/000788 WO2004002497A1 (fr) 2002-07-01 2003-06-24 Compositions contenant des glyco-alcaloides et leurs diverses utilisations

Country Status (5)

Country Link
EP (1) EP1539191A4 (fr)
AU (3) AUPS329002A0 (fr)
CA (1) CA2489675A1 (fr)
NZ (1) NZ537267A (fr)
WO (1) WO2004002497A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004062675A1 (fr) * 2003-01-15 2004-07-29 Solbec Pharmaceuticals Limited Procede de modulation de il-6
WO2006092017A1 (fr) * 2005-03-02 2006-09-08 Solbec Pharmaceuticals Limited Combinaisons d'un glycoalcaloïde et d'un agoniste de tlr et diverses applications desdites combinaisons
WO2008064425A1 (fr) * 2006-11-30 2008-06-05 Solbec Pharmaceuticals Limited Combinaisons de glycoalkaloïdes et d'agents chimiothérapeutiques et utilisations diverses
US7811781B2 (en) 2005-07-06 2010-10-12 Btg International Limited Core 2 β(1,6)-acetylglycosaminyltransferase as diagnostic marker for atherosclerosis
US7906493B2 (en) 2003-12-22 2011-03-15 Btg International Limited Core 2 GlcNAc-T inhibitors
US7998943B2 (en) 2005-07-06 2011-08-16 Btg International Limited Core 2 GlcNAc-T inhibitors III
US8197794B2 (en) 2003-12-22 2012-06-12 Ms Therapeutics Limited Core 2 GlcNAc-T inhibitors
EP2522357A1 (fr) * 2011-05-12 2012-11-14 G & E Herbal Biotechnology Co., Ltd. Traitement et/ou prévention de l'inflammation et des lésions cutanées causées par la lumière et photoprotection de la peau avec un extrait soluble dans l'eau d'une plante du genre solanum
CN102872260A (zh) * 2011-06-10 2013-01-16 德英生物科技股份有限公司 使用茄属植物的水溶性萃取物来治疗和/或预防发炎与皮肤光损害以及光防护皮肤
AU2012200389B2 (en) * 2011-05-04 2013-10-31 G & E Herbal Biotechnology Co., Ltd. Anti-wart pharmaceutical composition and method for treating wart
US8609633B2 (en) 2005-07-06 2013-12-17 Ms Therapeutics Limited Core 2 GlcNAc-T inhibitors
CN111303239A (zh) * 2020-03-02 2020-06-19 河南中医药大学 两种治疗食管癌的活性单体、组合物及其应用
CN114306361A (zh) * 2021-11-29 2022-04-12 成都大学 Khasianine在制备用于预防和/或治疗炎症性疾病药物中的用途

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU540812B2 (en) * 1979-05-02 1984-12-06 Aruba Qld Pty. Ltd. Steroid alkaloids
AU654474B2 (en) * 1990-01-18 1994-11-10 Cura Nominees Pty Ltd Glycoalkaloids
AU3545400A (en) * 1999-04-09 2000-11-14 Cura Nominees Pty Ltd Medicinal compositions and their method of preparation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ193564A (en) * 1979-05-02 1985-01-31 Aruba Pty Ltd Steroid alkaloids from solanum sodomeum and pharmaceutical compositions
ES2253566T3 (es) * 2001-09-28 2006-06-01 Glycomed Sciences Limited Procedimiento de extraccion con disolventes.

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU540812B2 (en) * 1979-05-02 1984-12-06 Aruba Qld Pty. Ltd. Steroid alkaloids
AU654474B2 (en) * 1990-01-18 1994-11-10 Cura Nominees Pty Ltd Glycoalkaloids
AU3545400A (en) * 1999-04-09 2000-11-14 Cura Nominees Pty Ltd Medicinal compositions and their method of preparation

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
CHAM B.E. ET AL.: "TOPICAL TREATMENT OF MALIGNANT AND PREMALIGNANT SKIN LESIONS BY VERY LOW CONCENTRATIONS OF A STANDARD MIXTURE (BEC) OF SOLASODINE GLYCOSIDES", CANCER LETTERS, vol. 59, 1991, pages 183 - 192, XP001077064 *
CHAM B.E.: "Monograph on the compound BEC", DRUGS OF THE FUTURE, vol. 13, no. 8, 1988, pages 714 - 716, XP008078899 *
CHAM B.E.: "SOLASODINE GLYCOSIDES AS ANTI-CANCER AGENTS: PRE-CLINICAL AND CLINICAL STUDIES", ASIA PACIFIC JOURNAL OF PHARMACOLOGY, vol. 9, 1994, pages 113 - 118, XP002950616 *
CHAM BILL E. ET AL.: "ANTITUMOUR EFFECTS OF GLYCOALKALOIDS ISOLATED FROM SOLANUM SODOMAEUM", PLANTA MEDICA, vol. 53, no. 1, 1987, pages 34 - 36, XP009023197 *
DAUNTER B. ET AL.: "Solasodine glycosides. In vitro preferential cytotoxicity for human cancer cells", CANCER LETTERS, vol. 55, no. 3, 1990, pages 209 - 220, XP003010332 *
GHOSH M. ET AL.: "ANTIFILARIAL EFFECT OF SOLAMARGINE ISOLATED FROM SLOANUM KHASIANUM", INT. J. PHARMACOGNOSY, vol. 32, no. 2, 1994, pages 184 - 190, XP009078694 *
LI-CHING CHANG ET AL.: "THE RHAMNOSE MOIETY OF SOLAMARGINE PLAYS A CRUCIAL ROLE IN TRIGGERING CELL DEATH BY APOPTOSIS", BIOCHEM. BIOPHYS. RESEARCH COMMUNICATIONS, vol. 242, no. 1, 1998, pages 21 - 25, XP002950617 *
See also references of EP1539191A4 *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004062675A1 (fr) * 2003-01-15 2004-07-29 Solbec Pharmaceuticals Limited Procede de modulation de il-6
US7906493B2 (en) 2003-12-22 2011-03-15 Btg International Limited Core 2 GlcNAc-T inhibitors
US8197794B2 (en) 2003-12-22 2012-06-12 Ms Therapeutics Limited Core 2 GlcNAc-T inhibitors
WO2006092017A1 (fr) * 2005-03-02 2006-09-08 Solbec Pharmaceuticals Limited Combinaisons d'un glycoalcaloïde et d'un agoniste de tlr et diverses applications desdites combinaisons
US7811781B2 (en) 2005-07-06 2010-10-12 Btg International Limited Core 2 β(1,6)-acetylglycosaminyltransferase as diagnostic marker for atherosclerosis
US7998943B2 (en) 2005-07-06 2011-08-16 Btg International Limited Core 2 GlcNAc-T inhibitors III
US8609633B2 (en) 2005-07-06 2013-12-17 Ms Therapeutics Limited Core 2 GlcNAc-T inhibitors
WO2008064425A1 (fr) * 2006-11-30 2008-06-05 Solbec Pharmaceuticals Limited Combinaisons de glycoalkaloïdes et d'agents chimiothérapeutiques et utilisations diverses
AU2012200389B2 (en) * 2011-05-04 2013-10-31 G & E Herbal Biotechnology Co., Ltd. Anti-wart pharmaceutical composition and method for treating wart
JP2012236815A (ja) * 2011-05-12 2012-12-06 G & E Herbal Biotechnology Co Ltd ナス属（ｓｏｌａｎｕｍｇｅｎｕｓ）植物からの水溶性抽出物での炎症及び皮膚の光損傷の治療及び／又は予防、並びに皮膚の光防護
EP2522357A1 (fr) * 2011-05-12 2012-11-14 G & E Herbal Biotechnology Co., Ltd. Traitement et/ou prévention de l'inflammation et des lésions cutanées causées par la lumière et photoprotection de la peau avec un extrait soluble dans l'eau d'une plante du genre solanum
US8614196B2 (en) 2011-05-12 2013-12-24 G & E Herbal Biotechnology Co., Ltd. Treatment and/or prevention of inflammation and cutaneous photodamage and photoprotection of the skin with a water-soluble extract from plant of Solanum genus
KR101397107B1 (ko) 2011-05-12 2014-05-19 지앤이 허벌 바이오테크놀로지 씨오., 엘티디. 솔라눔 속 식물의 수용성 추출물에 의한 염증 및 피부의 광손상 치료 및/또는 예방 및 피부의 광보호
CN102872260A (zh) * 2011-06-10 2013-01-16 德英生物科技股份有限公司 使用茄属植物的水溶性萃取物来治疗和/或预防发炎与皮肤光损害以及光防护皮肤
CN111303239A (zh) * 2020-03-02 2020-06-19 河南中医药大学 两种治疗食管癌的活性单体、组合物及其应用
CN111303239B (zh) * 2020-03-02 2022-03-01 河南中医药大学 两种治疗食管癌的活性单体、组合物及其应用
CN114306361A (zh) * 2021-11-29 2022-04-12 成都大学 Khasianine在制备用于预防和/或治疗炎症性疾病药物中的用途

Also Published As

Publication number Publication date
AUPS329002A0 (en) 2002-07-18
AU2009202266A1 (en) 2009-08-06
CA2489675A1 (fr) 2004-01-08
EP1539191A4 (fr) 2007-03-21
EP1539191A1 (fr) 2005-06-15
AU2003238544A1 (en) 2004-01-19
NZ537267A (en) 2006-11-30

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