EP1408913A2 - Analogues de prostaglandine destines a favoriser la croissance des cheveux - Google Patents

Analogues de prostaglandine destines a favoriser la croissance des cheveux

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Publication number
EP1408913A2
EP1408913A2 EP02768349A EP02768349A EP1408913A2 EP 1408913 A2 EP1408913 A2 EP 1408913A2 EP 02768349 A EP02768349 A EP 02768349A EP 02768349 A EP02768349 A EP 02768349A EP 1408913 A2 EP1408913 A2 EP 1408913A2
Authority
EP
European Patent Office
Prior art keywords
chain
straight
pgf
analogue
branched
Prior art date
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.)
Withdrawn
Application number
EP02768349A
Other languages
German (de)
English (en)
Inventor
Gerald D. Cagle
Michael V.W. Bergamini
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.)
Alcon Inc
Original Assignee
Alcon Inc
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 Alcon Inc filed Critical Alcon Inc
Publication of EP1408913A2 publication Critical patent/EP1408913A2/fr
Withdrawn legal-status Critical Current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
    • 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
    • A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • 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

Definitions

  • This invention relates to the use of certain prostaglandin analogues to promote the growth, thickness, and pigmentation of hair in mammals, including man.
  • the invention also relates to topical compositions for such use. More specifically, the invention relates to the use of certain FP prostaglandin analogues for the promotion of hair growth.
  • prostaglandin analogues originally developed as therapy for glaucoma, may also promote hair growth. See U.S. Patent Nos. 6,262,105 B1 and U.S. Patent Application Serial No. 09/774,555 (U.S. Patent Application Publication No. US 2002/0037914A1), the entire contents of both of which are by this reference incorporated herein.
  • U.S. Patent No. 6,262,105 (the '105 patent) was based in part on the observation that in some instances glaucoma patients receiving the prostaglandin analogue, latanoprost, experienced increased eyelash growth.
  • the patent broadly discloses the use of prostaglandins and prostaglandin analogues for enhancing hair growth, generically disclosing countless prostaglandin derivatives and analogues, as well as over a hundred specific compounds.
  • U.S. Patent Application Serial No. 09/774,555 discloses 5,6-13,14-tetrahydro PGF 2 ⁇ analogues (also characterized as 13,14- dihydro PGF ⁇ ⁇ analogues) for treating hair loss.
  • the compounds useful in the methods and compositions of the present invention are neither disclosed or suggested in the '555 application, nor are they encompassed within the scope of that application's broadest claims.
  • Cloprostenol and fluprostenol are synthetic analogues of PGF 2 ⁇ , a naturally-occurring F-series prostaglandin (PG). Structures for PGF 2 ⁇ (l), cloprostenol (II), and fluprostenol (III), are shown below:
  • cloprostenol The chemical name for cloprostenol is 16-(3-chlorophenoxy)-17,18,19,20- tetranor PGF 2 ⁇ .
  • Monograph No. 2461 page 407) of The Merck Index. 12th Edition (1996) is incorporated herein by reference to the extent that it describes the preparation and known pharmacological profiles of cloprostenol.
  • Fluprostenol has the chemical name 16-(3-trifluoromethylphenoxy)-17,18,19,20- tetranor PGF 2 ⁇ .
  • Monograph No. 4231 page 711) of The Merck Index. 12th Edition (1996) is incorporated herein by reference to the extent that it describes the preparation and known pharmacological profiles of fluprostenol.
  • Cloprostenol and fluprostenol are 16-aryloxy PGs differing from the natural product PGF 2 ⁇ by the substitution of a substituted phenoxy moiety for the last 4 carbons of the lower (omega) chain
  • the present invention relates to methods and compositions for the promotion of hair growth comprising certain PGF 2 ⁇ analogues and their pharmaceutically acceptable salts, esters, and amides.
  • PGF 2 ⁇ analogues and their pharmaceutically acceptable salts, esters, and amides.
  • Most preferred in such compositions and methods are potent and selective FP agonists selected from the group consisting of 9-deoxy, 11-oxa, 13-oxa, and 15-fluoro analogues of PGF 2 ⁇ , and the analogues described in U.S. Patent Nos. 5,510,383 and 5,889,052, previously incorporated by reference.
  • various pharmaceutically acceptable carriers suitable for topical administration are also known in topical administration.
  • — represents any combination of a single bond, or a cis or trans double bond for the alpha (upper) chain; and a single bond or trans double bond for the omega (lower) chain;
  • Rg H, C1-C10 straight-chain or branched alkyl, or C 1 -C 10 straight-chain or branched acyl;
  • R 1 OR or NR 3 R 4 , where
  • R H, a cationic salt moiety, a pharmaceutically acceptable amine moiety, or
  • R 5 H, alkyl, acyl, cycloalkyl, or aryl
  • R ⁇ CI or CF 3 .
  • esters of cloprostenol and fluprostenol which correspond to formula V wherein:
  • R C ⁇ -C 12 alkyl
  • R 2 CI or CF 3 .
  • 15-keto analogues of cloprostenol and fluprostenol are also preferred.
  • the generic name for the isopropyl ester of the preferred enantiomer of fluprostenol is travoprost. Travoprost, as well as fluprostenol and cloprostenol, and their 15-keto analogues are commercially available from Cayman Chemical Company, Ann Arbor, Michigan.
  • acyl represents a group that is linked by a carbon atom that has a double bond to an oxygen atom and single bond to another carbon atom.
  • alkenyl includes straight or branched chain hydrocarbon groups having 1 to 15 carbon atoms with at least one carbon-carbon double bond.
  • the chain hydrogens may be substituted with other groups, such as halogen.
  • Preferred straight or branched alkenyl groups include, allyl, 1-butenyl, 1-methyl-2-propenyl and 4-pentenyl.
  • alkoxy represents an alkyl group attached through an oxygen linkage.
  • alkyl includes straight or branched chain, saturated or unsaturated aliphatic hydrocarbon groups having 1 to 15 carbon atoms.
  • the alkyl groups may be substituted with other groups, such as halogen, hydroxyl or alkoxy.
  • Preferred straight or branched alkyl groups include lower alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl and f-butyl. Also included, however, are alkenyl and alkynyl groups.
  • alkynyl includes straight or branched chain hydrocarbon groups having 1 to 15 carbon atoms with at least one carbon-carbon triple bond.
  • the chain hydrogens may be substituted with other groups, such as halogen.
  • Preferred straight or branched alkynyl groups include, 2-propynyl, 2-butynyl, 3- butynyl, 1-methyl-2-propynyl and 2-pentynyl.
  • aryl refers to carbon-based rings which are aromatic.
  • the rings may be isolated, such as phenyl, or fused, such as naphthyl.
  • the ring hydrogens may be substituted with other groups, such as lower alkyl, or halogen.
  • aryl includes heteroaryl groups.
  • cationic salt moiety includes alkali and alkaline earth metal salts as well as ammonium salts.
  • cycloalkyl includes straight or branched chain, saturated or unsaturated aliphatic hydrocarbon groups which connect to form one or more rings, which can be fused or isolated.
  • the rings may be substituted with other groups, such as halogen, hydroxyl or lower alkyl.
  • Preferred cycloalkyl groups include cyclopropyl, cyclobutyl, cylopentyl and cyclohexyl.
  • heteroaryl refers to aromatic hydrocarbon rings which contain at least one heteroatom such as O, S, or N in the ring. Heteroaryl rings may be isolated, with 5 to 6 ring atoms, or fused, with 8 to 10 atoms.
  • the heteroaryl ring(s) hydrogens or heteroatoms with open valency may be substituted with other groups, such as lower alkyl or halogen. Examples of heteroaryl groups include imidazole, pyridine, indole, quinoline, furan, thiophene, pyrrole, tetrahydroquinoline, dihydrobenzofuran, and dihydrobenzindole.
  • lower alkyl represents alkyl groups containing one to six carbons (C- ⁇ -C 6 ).
  • Preferred among the compounds of Table 1 are those which are potent and selective FP receptor agonists; specifically, those for which the free acid form exhibits an FP binding IC 50 (based upon a travoprost 0.004% standard) of less than 1000 nM and/or greater than 50% agonistic activity (as reflected in Table 1 - travoprost acid representing the standard full agonist (100%); and most preferably those with IC 50 S less than 500 and/or agonistic activity greater than 75%.
  • Most preferred among the compounds of Table 1 are compounds 9, 18, 25, 42, 71 and 77, all of which are isopropyl esters.
  • the preferred isopropyl esters isopropyl esters will preferably be in enantiomerically pure form, which corresponds to compounds having the absolute stereochemical structure of PGF 2 ⁇ (I).
  • Topical formulations containing the prostaglandin analogues of the present invention for the treatment of glaucoma and ocular hypertension as well as methods of synthesizing and formulating the same are disclosed in U.S. Patent Nos. 5,510,383; 5,698,733; 5,889,052; 6,025,392; and 6,232,344; U.S. Patent Application Serial Nos. 09/284,432 and 10/100,399, the entire contents of which were previously incorporated by reference.
  • Storage-stable formulations and packaging systems for the compounds of the present invention are also described in U.S. Patent Nos. 5,631 ,287; 6,011 ,062; and 6,235,781 , the entire contents of each of which are by this reference incorporated herein.
  • the invention is also related to dermatological compositions for topical treatment for the stimulation of hair growth which comprise an effective hair growth stimulating amount of one or more prostaglandin analogues as defined above and a dermatologically compatible carrier.
  • Effective amounts of the active analogues will vary analogues on the derivative employed, frequency of application and desired result, but will generally range from about 0.0000001 to about 50% by weight of the dermatological composition; preferably from about 0.00001 to about 5% by weight; and most preferably from about 0.0001 to about 0.1% by weight.
  • compositions may thus comprise from about 0.001 to about 50 ⁇ g of the analogues in about 1 to about 100 ⁇ g of total dermatological composition, more preferably from about 0.01 to about 5 ⁇ g in about 10 to about 50 ⁇ g of the composition.
  • the compounds of the present invention are generally formulated as between about 0.00003 to about 3 percent by weight (wt%) solutions in water at a pH between 4.5 to 8.0.
  • the compounds are preferably formulated as between about 0.0003 to about 0.3 wt% and, most preferably, between about 0.003 and about 0.03 wt%. While the precise regimen is left to the discretion of the clinician, it is recommended that the resulting solution be topically applied by spray, roll-on or dropper and massaged into the affected area, for example the scalp, once a day.
  • ingredients which may be desirable to use in the dermatalogical preparations of the present invention include preservatives, co-solvents and viscosity building agents.
  • Dermatological products are typically packaged in multidose form, which generally require the addition of preservatives to prevent microbial contamination during use.
  • Suitable preservatives include: benzalkonium chloride, thimerosal, chlorobutanol, methyl paraben, propyl paraben, phenylethyl alcohol, edetate disodium, sorbic acid, ONAMER M®, or other agents known to those skilled in the art.
  • Such preservatives are typically employed at a concentration between about 0.001% and about 1.0% by weight.
  • Prostaglandins, and particularly ester derivatives typically have limited solubility in water and therefore may require a surfactant or other appropriate co- solvent in the composition.
  • co-solvents include: Polysorbate 20, 60 and 80; Pluronic F-68, F-84 and P-103; Tyloxapol ®; Cremophor® EL; sodium dodecyl sulfate; glycerol; PEG 400; propylene glycol; cyclodextrins; or other agents known to those skilled in the art.
  • co-solvents are typically employed at a concentration between about 0.01% and about 2% by weight.
  • Viscosity greater than that of simple aqueous solutions may be desirable to increase ocular absorption of the active compound, to decrease variability in dispensing the formulations, to decrease physical separation of components of a suspension or emulsion of formulation and/or otherwise to improve the ophthalmic formulation.
  • Such viscosity building agents include, for example, polyvinyl alcohol, polyvinyl pyrrolidone, methyl cellulose, hydroxy propyl methylcellulose, hydroxyethyl cellulose, carboxymethyl cellulose, hydroxy propyl cellulose or other agents known to those skilled in the art. Such agents are typically employed at a concentration between about 0.01% and about 2% by weight.
  • the individual enantiomers can be enantioselectively synthesized from the appropriate enantiomerically pure or enriched starting material by means such as those described below. Alternatively, they may be enantioselectively synthesized from racemic/non-racemic or achiral starting materials.
  • racemic and non-racemic mixtures may be obtained by several means, including without limitation, nonenantioselective synthesis, partial resolution or even mixing samples having different enantiomeric ratios. Also included within the scope of the present invention are the individual isomers substantially free of their respective enantiomers.
  • FP receptor binding assay The bovine corpus luteum has been shown to express high- affinity [ H]PGF 2 ⁇ binding sites, in addition to [ H]PGE 2 binding, which appear to have pharmacological characteristics of FP receptors. Washed total particulate bovine corpus luteum membranes (20 mg/ml final) were incubated with [ 3 H]PGF 2 ⁇ (0.9-1.5 nM) in Krebs buffer (pH 7.4) for 2 h at 23 ° C in a total volume of 500 ml. Non-specific binding was defined with 1-10 ⁇ M unlabeled PGF 2 ⁇ or fluprostenol. The assays were terminated by vacuum filtration (using Whatman GF/B glass fiber filter previously soaked in 0.3% polyethyleneimine) and the data analyzed by a non-linear, iterative, curve-fitting computer program.
  • FP receptor-mediated phosphoinositide turnover assay [ H]Inositol phosphates ([ H]- IPs) produced by agonist-mediated activation of phospholipase C in Swiss 3T3 cells expressing FP receptors were quantified as follows. Confluent 3T3 cells were exposed to 1.0 - 1.5 ⁇ Ci [ 3 H]-w O-inositol (18.3 Ci/mmol) in 0.5 ml DMEM for 24-30 hours at 37 ° C. Then cells were rinsed once with DMEM/F-12 containing 10 mM LiCl, and the agonist stimulation experiment was performed in 0.5 ml of the same medium to facilitate accumulation of [ 3 H]-IPs.
  • Cells were exposed to the agonist or solvent for 60 min at 37 ° C (triplicate determinations), followed by aspiration of the medium and immediate addition of 1 ml of ice-cold 0.1M formic acid. The plates were kept cold and then frozen. Samples frozen up to one week were thawed prior to chromatographic separation of radiolabeled components. The cell lysates (0.9 ml) were loaded on columns packed with approximately 1 ml AG 1-X8 anion exchange resin.
  • the elution procedure consisted of a wash with 10 ml of H O, then 8 ml of 50 mM ammonium formate, and finally 4 ml of 1.2M ammonium formate with 0.1 M formic acid, which was collected in a scintillation vial.
  • To this eluate was added 15 ml of scintillation fluid and the total [ 3 H]-IPs determined by scintillation counting on a beta-counter.
  • Data were analyzed by the sigmoidal fit function of the Origin Scientific Graphics software (Microcal Software, Northampton, MA) to determine agonist potency (EC 5 o value) and efficacy, relative to the standard cloprostenol.
  • Formulations 1-8 are representative pharmaceutical compositions of the invention for topical use in promoting hair growth. Each of Formulations 1 through 8 may be formulated in accordance with procedures known to those skilled in the art.
  • Eyelash photographs of each eye were taken at determination of patient eligibility 8AM (baseline) and Months 1.5, 3, 4.5 and 6 in four clinical studies. Additional photographs were taken at Months 9 and 12 in two clinical studies. Eyelash change was classified using the following categories: change in eyelash color, increase in eyelash length, increase in eyelash density and increase in eyelash thickness. Two independent readers evaluated the photographs subjectively for any change from baseline in eyelash characteristics. If the two readers did not agree, the photographs were evaluated by a third reader. In the case when all three readers had a different assessment, a meeting was held to come to a consensus. Eyelash changes from baseline evaluated by photographs were reported and are summarized in the following Table 3. Table 3
  • the majority of eyelash changes associated with travoprost (0.0015% and 0.004%) includes changes in color, and increases in length, density and/or thickness (Table 4). No clinically significant difference within a treatment group was observed for eyelash color, length, density and/or thickness. A concentration-related change in eyelash color, length, density and/or thickness was observed between patients receiving Travoprost 0.0015% and 0.004%. Patients receiving latanoprost 0.005% experienced similar types of changes in eyelash color, length, density, and/or thickness, but at a greatly reduced frequency compared to that of travoprost.
  • the compounds of the present invention may be formulated and applied as topical creams, ointments, solutions or suspensions, lotions, aerosols, dusting powders and the like.
  • the prostaglandin analogues of the present invention can be advantageously formulated using ointments, creams, liniments or patches as a carrier of the active ingredient.
  • these formulations may or may not contain preservatives, depending on the dispenser and nature of use. Such preservatives include those mentioned above, and methyl-, propyl-, or butyl- parahydroxybenzoic acid, betain, chlorhexidine, benzalkonium chloride, and the like.
  • Various matrices for slow release delivery may also be used.
  • the dose to be applied on the scalp is in the range of about 0.1 ng to about 100 mg per day, more preferably about 1 ng to about 10 mg per day, and most preferably about 10 ng to about 1 mg per day dependingn on the prostaglandin analogue and the formulation.
  • the prostaglandin analogue may be administered once or several times daily with or without antioxidants.
  • the compounds of the present invention, and especially travoprost or compound 42 may be substituted for the compounds described in examples 2-11 of the '105 patent.
  • the compounds of the present invention may be combined with one or more known agents for the promotion of hair growth. While bound by no theories, the inventors suspect that the mechanism of action by which the compounds of the present invention promote hair growth may be distinct from those of the presently available commercial hair growth products.
  • the compounds of the present invention may be combined with: i) minoxidil (Pharmacia) and minoxidil-type compounds; ii) finasteride (Merck) and finasteride-type compounds (dihydrotestosterone (DHT) blockers); and iii) copper-peptides or retinoic acid related compounds.
  • minoxidil-type compounds include: aminexil (Dercap) (L'Oreal); cromakalim/BRL 34915 (Pharmacia); diazoxide (Hyperstat IV, Proglycem); pinacidil; and its analogue PC-1075.
  • An example of a finasteride-type compound would be the herbal product Saw palmetto (serenoa repens), which acts as a DHT blocker.

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  • 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)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des procédés et des compositions comportant des analogues de PGF2α destinés à favoriser la croissance des cheveux chez les mammifères.
EP02768349A 2001-07-25 2002-07-25 Analogues de prostaglandine destines a favoriser la croissance des cheveux Withdrawn EP1408913A2 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US30783501P 2001-07-25 2001-07-25
US307835P 2001-07-25
US37330002P 2002-04-17 2002-04-17
US373300P 2002-04-17
PCT/US2002/023584 WO2003009820A2 (fr) 2001-07-25 2002-07-25 Analogues de prostaglandine destines a favoriser la croissance des cheveux

Publications (1)

Publication Number Publication Date
EP1408913A2 true EP1408913A2 (fr) 2004-04-21

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP02768349A Withdrawn EP1408913A2 (fr) 2001-07-25 2002-07-25 Analogues de prostaglandine destines a favoriser la croissance des cheveux

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EP (1) EP1408913A2 (fr)
JP (1) JP2004538288A (fr)
CA (1) CA2449462A1 (fr)
MX (1) MXPA04000712A (fr)
WO (1) WO2003009820A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007023841A1 (fr) * 2005-08-25 2007-03-01 Taisho Pharmaceutical Co., Ltd. Préparation d'agent pour la croissance des cheveux
FR2920309B1 (fr) * 2007-08-28 2010-05-28 Galderma Res & Dev Utilisation de travoprost pour traiter la chute des cheveux
KR20100099145A (ko) * 2007-10-31 2010-09-10 파멜라 립킨 프로스타글란딘 유사체 조성물 및 상피 관련 질환을 치료하는 방법
US8633310B2 (en) 2008-02-19 2014-01-21 Allergan, Inc. Therapeutic substituted lactams
PL2317971T3 (pl) 2008-03-19 2016-03-31 Ciro Caruso Kompozycja do stymulowania wzrostu rzęs, brwi i włosów
JP7141025B1 (ja) * 2021-11-11 2022-09-22 エルデシエロ プライベート リミテッド 化合物、組成物、方法、及び製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE266397T1 (de) * 1997-02-04 2004-05-15 Murray A Johnstone Verfahren zur förderung des haarwuchses und entwicklung des haarsystems
US20020172693A1 (en) * 2000-03-31 2002-11-21 Delong Michell Anthony Compositions and methods for treating hair loss using non-naturally occurring prostaglandins

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03009820A2 *

Also Published As

Publication number Publication date
MXPA04000712A (es) 2004-04-20
WO2003009820A3 (fr) 2003-04-24
WO2003009820A2 (fr) 2003-02-06
CA2449462A1 (fr) 2003-02-06
JP2004538288A (ja) 2004-12-24
WO2003009820B1 (fr) 2003-11-13

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