WO2004054567A1 - Use of carnitines for the prevention and/or treatment of disorders caused by the andropause - Google Patents

Use of carnitines for the prevention and/or treatment of disorders caused by the andropause Download PDF

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Publication number
WO2004054567A1
WO2004054567A1 PCT/IT2003/000757 IT0300757W WO2004054567A1 WO 2004054567 A1 WO2004054567 A1 WO 2004054567A1 IT 0300757 W IT0300757 W IT 0300757W WO 2004054567 A1 WO2004054567 A1 WO 2004054567A1
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WO
WIPO (PCT)
Prior art keywords
carnitine
therapy
day
mos
propionyl
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.)
Ceased
Application number
PCT/IT2003/000757
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English (en)
French (fr)
Inventor
Aleardo Koverech
Giorgio Cavallini
Giulio Biagiotti
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.)
Sigma Tau Industrie Farmaceutiche Riunite SpA
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Sigma Tau Industrie Farmaceutiche Riunite SpA
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
Priority to MXPA05006072A priority Critical patent/MXPA05006072A/es
Priority to JP2004560181A priority patent/JP4767542B2/ja
Priority to DK03780642T priority patent/DK1569635T3/da
Priority to SI200331543T priority patent/SI1569635T1/sl
Priority to EP03780642A priority patent/EP1569635B1/en
Priority to AU2003288739A priority patent/AU2003288739A1/en
Application filed by Sigma Tau Industrie Farmaceutiche Riunite SpA filed Critical Sigma Tau Industrie Farmaceutiche Riunite SpA
Priority to DE60326262T priority patent/DE60326262D1/de
Priority to US10/535,509 priority patent/US7956091B2/en
Priority to CA2507429A priority patent/CA2507429C/en
Publication of WO2004054567A1 publication Critical patent/WO2004054567A1/en
Anticipated expiration legal-status Critical
Priority to US12/076,256 priority patent/US7776913B2/en
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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/221—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
    • 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
    • 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
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • 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
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/26—Androgens

Definitions

  • the invention described herein relates to the use of acetyl L-carnitine and propionyl L-carnitine in combination for the preparation of a medicament for the prevention and/or treatment of disorders caused by the andropause.
  • age-related diseases are an expanding field of application owing to the rapid increase in the population aged over 60 (J. Urol, 163: 705-712, 2000).
  • Hormone treatment for andropause is not without its drawbacks; in J. Urol, 151: 54-61, 1994, and in J. Urol, 163: 705-712, 2000, in fact, it is reported that testosterone treatment cannot be given in the presence of asymptomatic or frank prostate cancer.
  • a composition is described consisting of L-carnitine, acetyl L-carnitine and propionyl L-carnitine, useful for athletes subjected to intense physical effort, or for asthenic individuals.
  • a dietetic composition is described, consisting of L-carnitine, acetyl L-carnitine and propionyl L-carnitine for the treatment of alcohol withdrawal syndrome.
  • propionyl L-carnitine and acetyl L-carnitine proves to possess a surprising curative effect on the disorders caused by the andropause.
  • the combination according to the invention does not present the side effects of the androgens described above and can also be used in the group of patients who cannot be treated with the above-mentioned androgens.
  • One object of the present invention then is the use of propionyl L- carnitine in combination with acetyl L-carnitine, or one of their pharmaceutically acceptable salts for the preparation of a medicament for the prevention and/or treatment of andropause symptoms caused by male ageing or by chemical or surgical castration, characterised by the following symptoms: reduced libido or sexual drive and erectile function, also during the night, depression of mood and lowering of intellectual activity and spatial orientation capacity, fatigue, irritability, reduced lean body mass, muscular capacity, mental concentration, and functioning of the hair-growing apparatus, increased visceral fat, atrophy of the skin, and reduced bone density resulting in osteopenia and osteoporosis.
  • the andropause is also defined as “androgen decline in the aging male” (ADAM), or “partial androgen deficiency of the aging male” (PAD AM).
  • a pharmaceutically acceptable salt of propionyl L- carnitine and acetyl L-carnitine is any salt of these compounds with an acid that does not give rise to unwanted toxic or side effects.
  • salts are, for example, chloride, bromide, orotate, acid aspartate, acid citrate, magnesium citrate, acid phosphate, fumarate and acid fumarate, magnesium fumarate, lactate, maleate and acid maleate, mucate, acid oxalate, pamoate, acid pamoate, acid sulphate, glucose phosphate, tartrate, acid tartrate, magnesium tartrate, 2-amino- ethane sulphonate, magnesium 2-amino-ethane sulphonate, choline tartrate and trichloroacetate .
  • Propionyl L-carnitine and acetyl L-carnitine can be in any form suitable for oral or parenteral administration to human subjects.
  • Propionyl L-carnitine and acetyl L-carnitine can be formulated together, as a mixture, or can be formulated separately (separate packs), using known methods. Propionyl L-carnitine and acetyl L- carnitine can be administered to an individual both when contained in a mixture and when packaged separately.
  • the combination according to the invention can be marketed as a health food supplement, nutritional supplement, or therapeutic product on sale with or without a compul- sory prescription.
  • the preparation of the combination according to the present invention when in unit dosage form, contains from 4.0 to 0.5 g of propionyl L- carnitine inner salt, and from 0.50 g to 4.0 g of acetyl L-carnitine inner salt, or an equimolar amount of one of their pharmaceutically acceptable salts.
  • the preferred preparation of the combination, in unit dosage form contains 2 g of propionyl L-carnitine inner salt, and 2 g of acetyl L- carnitine inner salt, or an equimolar amount of one of their pharmaceutically acceptable salts.
  • the patients were divided at random into 3 groups of 15 each.
  • the patients in the first group were administered testosterone undecanoate (Andriol R -Organon) 40 x 2 g/day, while those in the second group received propionyl L-carnitine 1+1 g/day associated with acetyl L- carnitine 1+1 g/day, and those in the third group vitamin C (Redoxon R -Roche) 500 mg/day as a placebo.
  • the above-mentioned compounds were presented to the patients in anonymous containers and administered for 6 months.
  • PSA prostate-specific antigen
  • Prostate volume (cm 3 ) as measured by suprapubic ultrasonography and calculated by means of the three diameters rule [Rigatti P., Scattoni V., PSA: Antigene prostatico specifico. Edizioni Medico Scientifiche (EDIMES) Pavia, 1997].
  • RI was calculated as follows: (PSV-EDV/EDV) xlOO (Urology, 1997: 49: 822-830).
  • Table 1 shows the mean PSA levels in the three patient groups before, during and after therapy with the combination according to the invention, with the reference compound (testosterone) and with a placebo.
  • PSA prostate-specific antigen
  • Table 2 presents the data for mean prostate volume values before, during and after therapy with testosterone, with the combination according to the invention and with placebo. Table 2.
  • Table 3 presents the data for peak systolic velocity (PSV) of the right cavernous artery of the penis before, during and after therapy with the combination according to the invention, with testosterone and with placebo.
  • PSV peak systolic velocity
  • Peak systolic velocity (PSV) (mean value in cm/sec) of the right cavernous artery of the penis as measured by dynamic colour Doppler ultrasonographybefore, during and after administration of testosterone undecanoate (40 x 2 mg/day), propionyl L-carnitine 1 2 g/day + acetyl L-carnitine 1 x 2 g/day or placebo for 6 months to three groups of 15 patients each.
  • Data are mean ⁇ standard deviation.
  • Peak systolic velocity (PSV) (mean value in cm/sec) of the left cavernous artery of the penis as measured by dynamic colour Doppler ultrasonography before, during and after administration of testosterone undecanoate (40 x 2 mg/day), propionyl L-carnitine 1 2 g/day + acetyl L- carnitine 1 2 g/day or placebo for 6 months to three groups of 15 patients each. Data are mean ⁇ standard deviation.
  • End-diastolic velocity (mean value in cm/sec) of the right cavernous artery of the penis as measured by dynamic colour Doppler ultrasonography before, during and after administration of testosterone undecanoate (40 x 2 mg/day), propionyl L-carnitine 1 x 2 g/day + acetyl L-carnitine 1 2 g/day or placebo for 6 months to three groups of 15 patients each. Data are mean ⁇ standard deviation.
  • End-diastolic veloicity (mean value in cm/sec) of the left cavernous artery of the penis as measured by dynamic colour Doppler ultrasonography before, during and after administration of testosterone undecanoate (40 x 2 mg/day), propionyl L-carnitine 1 x 2 g/day + acetyl L-carnitine 1 2 g/day or placebo for 6 months to three groups of 15 patients each.
  • Data are mean ⁇ standard deviation.
  • RI Resistance Index
  • RI Resistance Index
  • Table 9 presents the data for duration of full nocturnal erections in minutes recorded by Rigiscan for a period of 3 nights before, during and after therapy with the combination according to the invention, with testosterone and with placebo.
  • Table 10 presents the data for blood total testosterone levels before, during and after therapy with the combination according to the invention, with testosterone and with placebo. The treatment with the compounds tested induced no significant changes.
  • Table 12 presents the data for blood levels of LH before, during and after treatment with the combination according to the invention, with testosterone and with placebo.
  • Table 13 presents the data for blood prolactin levels before, during and after treatment with the combination according to the invention, with testosterone and with placebo. The results obtained show that the treatment did not induce any significant changes.
  • oral testosterone and the combination according to the invention are capable of increasing libido regardless of prolactin (a hormone an increase in which gives rise to a reduction of libido and vice versa).
  • Table 14 presents the scores on the International Index of Erectile Function questionnaire (IIEF-15) - "Erectile Function" section, before, during and after therapy with the combination according to the invention, with testosterone and with placebo.
  • Administration of the placebo induced no significant changes in scores.
  • Table 17 presents the scores on the International Index of Erectile Function questionnaire (IIEF-15) - "General Satisfaction" section, before, during and after therapy with the combination according to the invention, with testosterone and with placebo.
  • the administration of testosterone and placebo failed to induce any significant changes in scores.
  • Table 18 presents the scores on the International Index of Erectile Function questionnaire (IIEF-15) - "Orgasmic Function" section, before, during and after therapy with the combination according to the invention, with testosterone and with placebo.
  • the placebo did not induce any significant changes in score.
  • Table 19 presents the scores on the DMS III questionnaire before, during and after therapy with the combination according to the invention, with testosterone and with placebo.
  • Propionyl L-carnitine 1 x 2 Before therapy 6.3 ⁇ 1.1 g/day + During therapy 4.7 ⁇ 0.9 acetyl L-carnitine (3 mos)
  • Table 20 presents the scores on the fatigue scale questionnaire before, during and after therapy with the combination according to the invention, with testosterone and with placebo.
  • both testosterone and the combination according to the invention proved capable of attenuating the symptoms of andropause.
  • Neither of the compounds tested induced pathological changes affecting the cervico-urethral district.
  • testosterone as mentioned above, its use is still contraindicated in the case of disease of the prostate district as well as for the onset of troublesome adverse effects on the liver, on lipid status, on cardiovascular and prostate diseases, and on sleep and behavioural disorders.
  • the combination according to the invention may therefore be regarded as the drug of choice in the treatment of patients with symptoms associated with ageing, since, in addition to being more active than testosterone, it can be used in a larger number of patients.

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  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
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PCT/IT2003/000757 2002-12-13 2003-11-20 Use of carnitines for the prevention and/or treatment of disorders caused by the andropause Ceased WO2004054567A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DE60326262T DE60326262D1 (de) 2002-12-13 2003-11-20 Verwendung von carnitinen zur prävention und/oder behandlung von krankheiten die durch die andropause verursacht werden
JP2004560181A JP4767542B2 (ja) 2002-12-13 2003-11-20 男性更年期が原因の異常の予防および／または治療のためのカルニチンの使用
DK03780642T DK1569635T3 (da) 2002-12-13 2003-11-20 Anvendelse af carnitiner til forebyggelse og/eller behandling af lidelser forårsaget af andropause
SI200331543T SI1569635T1 (sl) 2002-12-13 2003-11-20 Uporaba karnitinov za preventivo in/ali zdravljenje motenj povzroäśenih z andropavzo
EP03780642A EP1569635B1 (en) 2002-12-13 2003-11-20 Use of carnitines for the prevention and/or treatment of disorders caused by the andropause
MXPA05006072A MXPA05006072A (es) 2002-12-13 2003-11-20 Usos de carnitinas para prevencion y/o tratamiento de trastornos provocados por la andropausia.
CA2507429A CA2507429C (en) 2002-12-13 2003-11-20 Use of carnitines for the prevention and/or treatment of disorders caused by the andropause
AU2003288739A AU2003288739A1 (en) 2002-12-13 2003-11-20 Use of carnitines for the prevention and/or treatment of disorders caused by the andropause
US10/535,509 US7956091B2 (en) 2002-12-13 2003-11-20 Use of carnitines for the prevention and/or treatment of disorders caused by the andropause
US12/076,256 US7776913B2 (en) 2002-12-13 2008-03-14 Carnitines for treating or preventing disorders caused by andropause

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITRM2002A000620 2002-12-13
IT000620A ITRM20020620A1 (it) 2002-12-13 2002-12-13 Uso delle carnitine per la prevenzione e/o il trattamento dei disturbi causati dall'andropausa.

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WO2004054567A1 true WO2004054567A1 (en) 2004-07-01

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PCT/IT2003/000757 Ceased WO2004054567A1 (en) 2002-12-13 2003-11-20 Use of carnitines for the prevention and/or treatment of disorders caused by the andropause

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US (1) US7956091B2 (enExample)
EP (1) EP1569635B1 (enExample)
JP (1) JP4767542B2 (enExample)
KR (1) KR101039818B1 (enExample)
AT (1) ATE422883T1 (enExample)
AU (1) AU2003288739A1 (enExample)
CA (1) CA2507429C (enExample)
CY (1) CY1109051T1 (enExample)
DE (1) DE60326262D1 (enExample)
DK (1) DK1569635T3 (enExample)
ES (1) ES2322455T3 (enExample)
IT (1) ITRM20020620A1 (enExample)
MX (1) MXPA05006072A (enExample)
PL (1) PL211032B1 (enExample)
PT (1) PT1569635E (enExample)
SI (1) SI1569635T1 (enExample)
WO (1) WO2004054567A1 (enExample)

Cited By (5)

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Publication number Priority date Publication date Assignee Title
WO2006050794A1 (en) * 2004-11-11 2006-05-18 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Use of acetyl l-carnitine in combination with propionyl l-carnitine and sildenafil for the treatment of erectile dysfunction
WO2006116630A3 (en) * 2005-04-27 2007-02-01 Jay M D W Pettegrew Method for use of acetyl-l-carnitine ( alcar) for treatment of depressive disorders in humans
US7407778B2 (en) 2002-02-07 2008-08-05 Pettegrew Jay W Compounds, compositions and methods for treating neuropsychiatric disorders
US7700074B2 (en) 2002-02-07 2010-04-20 Pettegrew Jay W Method and system for diagnosis of neuropsychiatric disorders including chronic alcoholism
US7815894B2 (en) 2003-05-29 2010-10-19 Jay W. Pettegrew Compounds, compositions and methods for medical imaging of neuropsychiatric disorders

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101460125B1 (ko) * 2013-02-05 2014-11-11 주식회사 바이오그랜드 루이보스 추출물을 유효성분으로 하는 남성 노화 및 갱년기 예방 및 개선용 조성물
WO2016167254A1 (ja) * 2015-04-17 2016-10-20 株式会社山田養蜂場本社 蜂の子を含有する滋養強壮剤

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7407778B2 (en) 2002-02-07 2008-08-05 Pettegrew Jay W Compounds, compositions and methods for treating neuropsychiatric disorders
US7700074B2 (en) 2002-02-07 2010-04-20 Pettegrew Jay W Method and system for diagnosis of neuropsychiatric disorders including chronic alcoholism
US7815894B2 (en) 2003-05-29 2010-10-19 Jay W. Pettegrew Compounds, compositions and methods for medical imaging of neuropsychiatric disorders
WO2006050794A1 (en) * 2004-11-11 2006-05-18 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Use of acetyl l-carnitine in combination with propionyl l-carnitine and sildenafil for the treatment of erectile dysfunction
JP2008531466A (ja) * 2004-11-11 2008-08-14 シグマ−タウ・インドゥストリエ・ファルマチェウチケ・リウニテ・ソシエタ・ペル・アチオニ 勃起不全の治療のためのプロピオニルｌ−カルニチンおよびシルデナフィルと組み合わせてのアセチルｌ−カルニチンの使用
US8003652B2 (en) 2004-11-11 2011-08-23 Sigma-Tau Industrie Farmaceutiche Riunite, S.P.A. Use of acetyl L-carnitine in combination with propionyl L-carnitine and Sildenafil for the treatment of erectile dysfunction
WO2006116630A3 (en) * 2005-04-27 2007-02-01 Jay M D W Pettegrew Method for use of acetyl-l-carnitine ( alcar) for treatment of depressive disorders in humans

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JP2006511531A (ja) 2006-04-06
MXPA05006072A (es) 2005-09-30
US20060135606A1 (en) 2006-06-22
CA2507429C (en) 2012-09-04
KR20050084052A (ko) 2005-08-26
ITRM20020620A1 (it) 2004-06-14
ES2322455T3 (es) 2009-06-22
DK1569635T3 (da) 2009-04-20
CA2507429A1 (en) 2004-07-01
EP1569635A1 (en) 2005-09-07
EP1569635B1 (en) 2009-02-18
ATE422883T1 (de) 2009-03-15
AU2003288739A1 (en) 2004-07-09
SI1569635T1 (sl) 2009-06-30
PL211032B1 (pl) 2012-04-30
US7956091B2 (en) 2011-06-07
JP4767542B2 (ja) 2011-09-07
PL378418A1 (pl) 2006-04-03
KR101039818B1 (ko) 2011-06-09
DE60326262D1 (de) 2009-04-02
CY1109051T1 (el) 2014-07-02

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