WO1997025034A1 - Use of the l-enantiomer of centchroman for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of breast cancer - Google Patents
Use of the l-enantiomer of centchroman for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of breast cancer Download PDFInfo
- Publication number
- WO1997025034A1 WO1997025034A1 PCT/DK1997/000007 DK9700007W WO9725034A1 WO 1997025034 A1 WO1997025034 A1 WO 1997025034A1 DK 9700007 W DK9700007 W DK 9700007W WO 9725034 A1 WO9725034 A1 WO 9725034A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- breast cancer
- enantiomer
- treatment
- phenyl
- pharmaceutically acceptable
- Prior art date
Links
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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- 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 relates to the use of the isolated l-enantiomer of centchro ⁇ man (3,4-trans-2,2-dimethyl-3-phenyl-4-[4-(2-(pyrrolidin-1 -yl)ethoxy)phenyl]-7- methoxychroman) or pharmaceutically acceptable salts thereof for the treatment of patients suffering from breast cancer and prophylaxis hereof.
- the present in- vention also embraces pharmaceutical compositions comprising the l-enantiomer of centchroman or pharmaceutically acceptable salts thereof and methods of using above mentioned compounds and their pharmaceutical compositions.
- breast cancer is the most common malignant tumor and the leading cause of cancer death in women. It causes approximately 20% of the cancer deaths among women. However, in spite of many years of intensive research and new types of treatment the age-adjusted death rate from breast cancer in the western world has virtually remained stable over the past 30 years.
- the term " breast cancer” implies a carcinoma arising in the ductal and glandular structures of the breast. Breast cancer is rare in women who have been castrated; oophorectomy before 35 years of age reduces the risk to one third. Women who have their first child before the age of 1 8 years have only one third the risk compared with those whose first child is delayed until age 30. Growth of breast cancer is associated with the presence of estrogen.
- a course of treatment of breast cancer is, therefore, ablation of the estrogen source by ovariectomy or hysterectomy.
- An alternative to this surgical approach is endocrine therapy whereby an estrogen antagonist is used to deplete estrogen concentration at the target site.
- Centchroman is a non-steroidal compound known to have antiestrogenic activity. It is in use in India as an oral contraceptive (see, for example, Salman et al., U.S. Patent Specification No. 4,447,622; Singh et al., Acta Endocrinol.
- Centchroman has also been investigated as an anti-cancer agent for treatment of advanced breast cancer (Misra et al., ]ni. J. Cancer 43 (1 989), 781 - 783). Recently, centchroman as a racemate has been found as a potent cholesterol lowering pharmaceutical expressed by a significant decrease of the serum concentrations (S.D. Bain et al., J.Min.Bon.Res. 9. (1 994), 394). However, it has never been disclosed that the isolated l-enantiomer of centchroman is use ⁇ ful for treatment of breast cancer.
- compositions and methods that are useful and safe in the treatment or prophylaxis of breast cancer.
- One object of the present invention is to provide compounds which can effecti ⁇ vely be used in the treatment or prophylaxis of breast cancer.
- the present invention relates to the use of the isolated l-enantiomer of centchro- man (3,4-trans-2,2-dimethyl-3-phenyl-4-[4-(2-(pyrrolidin-1 -yl)ethoxy)phenyl]-7- methoxychroman) or pharmaceutically acceptable salts thereof for the manufac ⁇ ture of a pharmaceutical composition for the treatment or prophylaxis of breast cancer.
- 3,4-diarylchromans are prepared according to known methods, such as those disclosed in U .S. Patent Specification No. 3,340,276 to Carney et al., U.S. Patent Specification No. 3,822,287 to Bolger, and Ray et al., J. ed.Chem. 1_ ⁇ ( 1 976), 276 - 279, the contents of which are incorporated herein by reference. Conversion of the cis isomer to the trans configuration by means of an organo- metallic base-catalyzed rearrangement is disclosed in U.S. Patent Specification No. 3,822,287.
- the optically active d- and l-enantiomers may be prepared as disclosed by Salman et al. in U.S. Patent Specification No. 4,447,622
- the l-enantiomer of centchroman may be prepared in the form of pharmaceutically acceptable salts, especially acid-addition salts, in ⁇ cluding salts of organic acids and mineral acids.
- salts include salts of organic acids such as formic acid, fumaric acid, acetic acid, propionic acid, glycolic acid, lactic acid, pyruvic acid, oxalic acid, succinic acid, malic acid, tartaric acid, citric acid, benzoic acid, salicylic acid and the like.
- Suitable inorga- nic acid-addition salts include salts of hydrochloric, hydrobromic, sulphuric and phosphoric acids and the like.
- the acid addition salts may be obtained as the direct products of compound synthesis.
- the free base may be dissolved in a suitable solvent containing the appropriate acid, and the salt isolated by evaporating the solvent or otherwise separating the salt and solvent.
- the l-enantiomer of centchroman and its salts are useful within human and vete ⁇ rinary medicine, for example, in the treatment of patients suffering from breast cancer.
- the l-enantiomer of centchroman or its pharmaceutically acceptable salts are formulated with a pharmaceutically acceptable carrier to provide a medicament for parenteral, oral, nasal, rectal, subdermal or intradermal or transdermal administration according to conventional methods.
- Formulations may further include one or more diluents, fillers, emulsi ⁇ fiers, preservatives, buffers, excipients, etc.
- centchroman may be provided in such forms as liquids, powders, emulsions, suppositories, liposomes, transdermal patches, controlled release, dermal implants, tablets, etc.
- One skilled in this art may for ⁇ mulate the l-enantiomer of centchroman or a pharmaceutically acceptable salt thereof in an appropriate manner, and in accordance with accepted practices, such as those disclosed in Remington's Pharmaceutical Sciences. Gennaro, ed., Mack Publishing Co., Easton, PA, 1 990
- the active l-enantiomer of centchroman or a pharmaceutically acceptable salt thereof is prepared in a form suitable for oral administration, such as a tablet or capsule.
- a pharmaceutically acceptable salt of the l-enantiomer of centchroman is combined with a carrier and moulded into a tablet.
- Suitable carriers include starch, sugars, dicalcium phosphate, calcium stearate, magnesium stearate and the like.
- Such compositions may further include one or more auxiliary substances, such as wetting agents, emulsifiers, preservatives, stabilizers, colouring additives, etc.
- compositions containing a compound of the l-enantiomer of centchroman or a pharmaceutically acceptable salt thereof is administered one or more times per day or week.
- An effective amount of such a pharmaceutical composition is the amount that provides a clinically significant effect against breast cancer. Such amounts will depend, in part, on the particular condition to be treated, age, weight, and general health of the patient, and other factors evi ⁇ dent to those skilled in the art.
- a typical daily dose will contain a non-toxic dosage range of from about 0 001 to about 75 mg/kg patient per day of a compound of the present invention
- compositions containing the l-enantiomer of centchroman or a pharmaceutically acceptable salt thereof may be administered in unit dosage form one or more times per day or week.
- they may be pro ⁇ vided as controlled release formulations suitable for dermal implantation.
- Im ⁇ plants are formulated to provide release of active compound over the desired period of time, which can be up to several years.
- Controlled-release formulations are disclosed by, for example, Sanders et al., J.Pharm.Sci. 23. ( 1 964), 1 294 - 1 297, 1 984; U.S. Patent Specification No 4,489,056; and U.S. Patent Specifi ⁇ cation No. 4,21 0,644, which are incorporated herein by reference.
- the present invention is further illustrated by the following examples which, however, are not to be construed as limiting the scope of protection.
- mice Between 1 5 and 45 nude (thymus deficient) mice are ovariectomized under phe- nobarbital anaesthesia. After one week recovery an estrogen sensitive human tumor cell line (MCF7, mammary cancer fibroblast 7) is serially transplanted to each of these animals. Subsequently the mice are treated with either placebo (negative control), 1 7-beta-estradiol (positive control), or the test compound. Oestrogen stimulated tumor growth is assessed by measurement of tumor size twice weekly for a dosing period of approximately 8 weeks.
- MCF7 estrogen sensitive human tumor cell line
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR9706966A BR9706966A (pt) | 1996-01-11 | 1997-01-09 | Utilização do enanciômero-l de um composto e processo para tratamento ou profilaxia de câncer da mama |
IL12488197A IL124881A0 (en) | 1996-01-11 | 1997-01-09 | Use of the l-enantiomer of centchroman for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of breast cancer |
AU13671/97A AU1367197A (en) | 1996-01-11 | 1997-01-09 | Use of the l-enantiomer of centchroman for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of breast cancer |
EP97900199A EP0873119A1 (en) | 1996-01-11 | 1997-01-09 | Use of the l-enantiomer of centchroman for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of breast cancer |
JP09524767A JP2001500101A (ja) | 1996-01-11 | 1997-01-09 | 乳癌の治療及び予防のための医薬組成物の製造のためのセントクロマンのl―鏡像異性体の使用 |
PL97328135A PL328135A1 (en) | 1996-01-11 | 1997-01-09 | Application of 1-centchromane enantiomer in production of a pharmaceutic agent for preventing or treating mammary cancers |
NO983177A NO983177L (no) | 1996-01-11 | 1998-07-10 | Anvendelse av 1-enantiomeren av centkroman til fremstilling av et farmasaytisk preparat for behandling eller profylakse av brystkreft |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1000096P | 1996-01-11 | 1996-01-11 | |
US60/010,000 | 1996-01-11 | ||
DK77696 | 1996-07-11 | ||
DK0776/96 | 1996-07-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997025034A1 true WO1997025034A1 (en) | 1997-07-17 |
Family
ID=26064631
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/DK1997/000007 WO1997025034A1 (en) | 1996-01-11 | 1997-01-09 | Use of the l-enantiomer of centchroman for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of breast cancer |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP0873119A1 (no) |
JP (1) | JP2001500101A (no) |
KR (1) | KR19990077157A (no) |
AU (1) | AU1367197A (no) |
BR (1) | BR9706966A (no) |
CA (1) | CA2241462A1 (no) |
CZ (1) | CZ217198A3 (no) |
HU (1) | HUP9901633A3 (no) |
IL (1) | IL124881A0 (no) |
NO (1) | NO983177L (no) |
PL (1) | PL328135A1 (no) |
WO (1) | WO1997025034A1 (no) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999024032A1 (en) * | 1997-11-10 | 1999-05-20 | Novo Nordisk A/S | Transdermal delivery of 3,4-diarylchromans |
US6465445B1 (en) | 1998-06-11 | 2002-10-15 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
AU2004200099B2 (en) * | 1998-06-11 | 2006-11-02 | Endorecherche, Inc. | Medical Uses of A Selective Estrogen Receptor Modulator in Combination with Sex Steroid Precursors |
US8268806B2 (en) | 2007-08-10 | 2012-09-18 | Endorecherche, Inc. | Pharmaceutical compositions |
US8389548B2 (en) | 1998-06-11 | 2013-03-05 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
WO2013130832A1 (en) | 2012-02-29 | 2013-09-06 | Repros Therapeutics Inc. | Combination therapy for treating androgen deficiency |
AU2011253842B2 (en) * | 1998-06-11 | 2014-08-14 | Endorecherche Inc. | Medical Uses of a Selective Estrogen Receptor Modulator in Combination with Sex Steroid Precursors |
US8835413B2 (en) | 2004-10-20 | 2014-09-16 | Endorecherche, Inc. | Sex steroid precursors alone or in combination with a selective estrogen receptor modulator and/or with estrogens and/or a type 5 cGMP phosphodiesterase inhibitor for the prevention and treatment of vaginal dryness and sexual dysfunction in postmenopausal women |
EP2826475A1 (en) | 2007-10-16 | 2015-01-21 | Repros Therapeutics Inc. | Trans-clomiphene for treating diabetes in hypogonadal men |
WO2015135061A1 (en) | 2014-03-10 | 2015-09-17 | Endorecherche, Inc. | Treatment of male androgen deficiency symptoms or diseases with sex steroid precursor combined with serm |
WO2017081171A1 (en) | 2015-11-10 | 2017-05-18 | Paracrine Therapeutics Ab | Treatment of er-negative breast cancer with an pdgf-cc inhibitor and an anti estrogen |
EP3178480A1 (en) | 2009-06-16 | 2017-06-14 | Endorecherche, Inc. | Treatment of hot flushes, vasomotor symptoms, and night sweats with sex steroid precursors in combination with selective estrogen receptor modulators |
US11576891B2 (en) | 2010-06-16 | 2023-02-14 | Endorecherche, Inc. | Methods of treating or preventing estrogen-related diseases |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4447622A (en) * | 1981-09-22 | 1984-05-08 | Council Of Scientific And Industrial Research Rafi Marg | Preparation of l- and d-isomers of dl-3,4-trans-2,2-disubstituted-3,4-diarylchromans and derivatives thereof |
-
1997
- 1997-01-09 WO PCT/DK1997/000007 patent/WO1997025034A1/en not_active Application Discontinuation
- 1997-01-09 JP JP09524767A patent/JP2001500101A/ja active Pending
- 1997-01-09 HU HU9901633A patent/HUP9901633A3/hu unknown
- 1997-01-09 CZ CZ982171A patent/CZ217198A3/cs unknown
- 1997-01-09 CA CA002241462A patent/CA2241462A1/en not_active Abandoned
- 1997-01-09 PL PL97328135A patent/PL328135A1/xx unknown
- 1997-01-09 AU AU13671/97A patent/AU1367197A/en not_active Abandoned
- 1997-01-09 EP EP97900199A patent/EP0873119A1/en not_active Withdrawn
- 1997-01-09 BR BR9706966A patent/BR9706966A/pt not_active Application Discontinuation
- 1997-01-09 IL IL12488197A patent/IL124881A0/xx unknown
- 1997-01-09 KR KR1019980705295A patent/KR19990077157A/ko not_active Application Discontinuation
-
1998
- 1998-07-10 NO NO983177A patent/NO983177L/no unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4447622A (en) * | 1981-09-22 | 1984-05-08 | Council Of Scientific And Industrial Research Rafi Marg | Preparation of l- and d-isomers of dl-3,4-trans-2,2-disubstituted-3,4-diarylchromans and derivatives thereof |
Non-Patent Citations (1)
Title |
---|
INT. J. CANCER, Volume 43, 1989, N.C. MISRA et al., "Centchroman-A Non-Steroidal Anti-Cancer Agent for Advanced Breast Cancer: Phase-II Study", pages 781-783. * |
Cited By (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999024032A1 (en) * | 1997-11-10 | 1999-05-20 | Novo Nordisk A/S | Transdermal delivery of 3,4-diarylchromans |
EP2386305A2 (en) | 1998-06-11 | 2011-11-16 | Endorecherche Inc. | Selective Estrogen Receptor Modulator in Combination With Dehydroepiandrosterone (DHEA) or Analogues |
EP2399582A1 (en) | 1998-06-11 | 2011-12-28 | Endorecherche Inc. | Selective Estrogen Receptor Modulator in Combination With Dehydroepiandrosterone (DHEA) or Analogues |
EP1083905B1 (en) * | 1998-06-11 | 2005-11-02 | Endorecherche Inc. | Medical use of a selective estrogen receptor modulator in combination with a sex steroide precursor |
AU2004200099B2 (en) * | 1998-06-11 | 2006-11-02 | Endorecherche, Inc. | Medical Uses of A Selective Estrogen Receptor Modulator in Combination with Sex Steroid Precursors |
US7429576B2 (en) | 1998-06-11 | 2008-09-30 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
US7943603B2 (en) | 1998-06-11 | 2011-05-17 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
US6670346B1 (en) | 1998-06-11 | 2003-12-30 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
AU2011253842B2 (en) * | 1998-06-11 | 2014-08-14 | Endorecherche Inc. | Medical Uses of a Selective Estrogen Receptor Modulator in Combination with Sex Steroid Precursors |
EP2386304A2 (en) | 1998-06-11 | 2011-11-16 | Endorecherche Inc. | Selective Estrogen Receptor Modulator in Combination With Dehydroepiandrosterone (DHEA) or Analogues |
US8188066B2 (en) | 1998-06-11 | 2012-05-29 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
US6465445B1 (en) | 1998-06-11 | 2002-10-15 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
US8389548B2 (en) | 1998-06-11 | 2013-03-05 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
US10076525B2 (en) | 2004-10-20 | 2018-09-18 | Endorecherche, Inc. | Sex steroid precursors alone or in combination with selective estrogen receptor modulators for the prevention and treatment of dyspareunia in postmenopausal women |
US10478443B2 (en) | 2004-10-20 | 2019-11-19 | Endorecherche, Inc. | Sex steroid precursors alone or in combination with selective estrogen receptor modulators for the prevention and treatment of sexual dysfunction in postmenopausal women |
US8835413B2 (en) | 2004-10-20 | 2014-09-16 | Endorecherche, Inc. | Sex steroid precursors alone or in combination with a selective estrogen receptor modulator and/or with estrogens and/or a type 5 cGMP phosphodiesterase inhibitor for the prevention and treatment of vaginal dryness and sexual dysfunction in postmenopausal women |
US8629129B2 (en) | 2007-08-10 | 2014-01-14 | Endorecherche, Inc. | Pharmaceutical compositions |
US8957054B2 (en) | 2007-08-10 | 2015-02-17 | Endorecherche, Inc. | Pharmaceutical compositions |
US10881650B2 (en) | 2007-08-10 | 2021-01-05 | Endorecherche, Inc. | Pharmaceutical compositions |
US8268806B2 (en) | 2007-08-10 | 2012-09-18 | Endorecherche, Inc. | Pharmaceutical compositions |
EP2826475A1 (en) | 2007-10-16 | 2015-01-21 | Repros Therapeutics Inc. | Trans-clomiphene for treating diabetes in hypogonadal men |
EP3682880A1 (en) | 2009-06-16 | 2020-07-22 | Endorecherche, Inc. | Treatment of hot flushes, vasomotor symptoms, and night sweats with sex steroid precursors in combination with selective estrogen receptor modulators |
US11452731B2 (en) | 2009-06-16 | 2022-09-27 | Endorecherche, Inc. | Method of treating and preventing loss of cognition |
EP3178480A1 (en) | 2009-06-16 | 2017-06-14 | Endorecherche, Inc. | Treatment of hot flushes, vasomotor symptoms, and night sweats with sex steroid precursors in combination with selective estrogen receptor modulators |
US10342805B2 (en) | 2009-06-16 | 2019-07-09 | Endorecherche, Inc. | Treatment of Alzheimer's disease, loss of cognition, memory loss and dementia with sex steroid precursors in combination with selective estrogen receptor modulators |
US11576891B2 (en) | 2010-06-16 | 2023-02-14 | Endorecherche, Inc. | Methods of treating or preventing estrogen-related diseases |
WO2013130832A1 (en) | 2012-02-29 | 2013-09-06 | Repros Therapeutics Inc. | Combination therapy for treating androgen deficiency |
US10548903B2 (en) | 2014-03-10 | 2020-02-04 | Endorecherche, Inc. | Treatment of male androgen deficiency symptoms or diseases with sex steroid precursor combined with SERM |
US9744177B2 (en) | 2014-03-10 | 2017-08-29 | Endorecherche, Inc. | Treatment of male androgen deficiency symptoms or diseases with sex steroid precursor combined with SERM |
WO2015135061A1 (en) | 2014-03-10 | 2015-09-17 | Endorecherche, Inc. | Treatment of male androgen deficiency symptoms or diseases with sex steroid precursor combined with serm |
WO2017081171A1 (en) | 2015-11-10 | 2017-05-18 | Paracrine Therapeutics Ab | Treatment of er-negative breast cancer with an pdgf-cc inhibitor and an anti estrogen |
Also Published As
Publication number | Publication date |
---|---|
KR19990077157A (ko) | 1999-10-25 |
NO983177L (no) | 1998-07-10 |
AU1367197A (en) | 1997-08-01 |
CA2241462A1 (en) | 1997-07-17 |
BR9706966A (pt) | 1999-05-04 |
HUP9901633A2 (hu) | 1999-10-28 |
CZ217198A3 (cs) | 1998-11-11 |
PL328135A1 (en) | 1999-01-18 |
JP2001500101A (ja) | 2001-01-09 |
IL124881A0 (en) | 1999-01-26 |
EP0873119A1 (en) | 1998-10-28 |
HUP9901633A3 (en) | 2000-02-28 |
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