CA2346034A1 - 2, 4-pentadienoic acid derivatives having selective activity for retinoid x (rxr) receptors - Google Patents
2, 4-pentadienoic acid derivatives having selective activity for retinoid x (rxr) receptors Download PDFInfo
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- CA2346034A1 CA2346034A1 CA002346034A CA2346034A CA2346034A1 CA 2346034 A1 CA2346034 A1 CA 2346034A1 CA 002346034 A CA002346034 A CA 002346034A CA 2346034 A CA2346034 A CA 2346034A CA 2346034 A1 CA2346034 A1 CA 2346034A1
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- 230000000694 effects Effects 0.000 title abstract description 48
- 150000004492 retinoid derivatives Chemical class 0.000 title abstract description 41
- SDVVLIIVFBKBMG-ONEGZZNKSA-N (E)-penta-2,4-dienoic acid Chemical class OC(=O)\C=C\C=C SDVVLIIVFBKBMG-ONEGZZNKSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 285
- 125000003118 aryl group Chemical group 0.000 claims abstract description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 41
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims abstract 2
- -1 5 or 6 membered heteroaryl radical Chemical class 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 7
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
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- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical group C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 113
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
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- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/48—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
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- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Nutrition Science (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Toxicology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/164,950 US6147224A (en) | 1998-10-01 | 1998-10-01 | 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
| US09/164,950 | 1998-10-01 | ||
| PCT/US1999/021712 WO2000020370A1 (en) | 1998-10-01 | 1999-09-20 | 2, 4-pentadienoic acid derivatives having selective activity for retinoid x (rxr) receptors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2346034A1 true CA2346034A1 (en) | 2000-04-13 |
Family
ID=22596791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002346034A Abandoned CA2346034A1 (en) | 1998-10-01 | 1999-09-20 | 2, 4-pentadienoic acid derivatives having selective activity for retinoid x (rxr) receptors |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6147224A (enExample) |
| EP (2) | EP1117628B1 (enExample) |
| JP (1) | JP2002526516A (enExample) |
| KR (2) | KR20010075457A (enExample) |
| CN (1) | CN1328538A (enExample) |
| AR (1) | AR020691A1 (enExample) |
| AT (1) | ATE254593T1 (enExample) |
| AU (1) | AU757932B2 (enExample) |
| BR (1) | BR9914256A (enExample) |
| CA (1) | CA2346034A1 (enExample) |
| DE (1) | DE69912973T2 (enExample) |
| ES (1) | ES2207339T3 (enExample) |
| NZ (1) | NZ510528A (enExample) |
| TW (1) | TW580494B (enExample) |
| WO (1) | WO2000020370A1 (enExample) |
| ZA (1) | ZA200102635B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6566372B1 (en) | 1999-08-27 | 2003-05-20 | Ligand Pharmaceuticals Incorporated | Bicyclic androgen and progesterone receptor modulator compounds and methods |
| MXPA02002032A (es) | 1999-08-27 | 2003-05-19 | Ligand Pharm Inc | Compuestos moduladores del receptor de androgeno y metodos. |
| EP1212322A2 (en) | 1999-08-27 | 2002-06-12 | Ligand Pharmaceuticals Incorporated | 8-substituted-6-trifluoromethyl-9-pyrido[3,2-g]quinoline compounds as androgen receptor modulators |
| US6593493B1 (en) | 1999-09-14 | 2003-07-15 | Ligand Pharmaceuticals, Inc. | RXR modulators with improved pharmacologic profile |
| US6906046B2 (en) | 2000-12-22 | 2005-06-14 | Celltech R & D Inc. | Pharmaceutical uses and synthesis of benzobicyclooctanes |
| CA2442366C (en) * | 2001-03-27 | 2012-09-25 | Circagen Pharmaceutical, Llc | Histone deacetylase inhibitors |
| US8026280B2 (en) | 2001-03-27 | 2011-09-27 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| US7312247B2 (en) | 2001-03-27 | 2007-12-25 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| US6495719B2 (en) | 2001-03-27 | 2002-12-17 | Circagen Pharmaceutical | Histone deacetylase inhibitors |
| US7842727B2 (en) | 2001-03-27 | 2010-11-30 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| US6388105B1 (en) * | 2001-09-27 | 2002-05-14 | Allergan Sales, Inc. | Benzofuran, indole or benzothiophene 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
| US6720423B2 (en) | 2002-04-30 | 2004-04-13 | Allergan, Inc. | Dihydrobenzofuran and dihydrobenzothiophene 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
| EP1511477A4 (en) | 2002-05-22 | 2008-04-09 | Errant Gene Therapeutics Llc | HISTONE DEACETYLASE INHIBITORS BASED ON ALPHA-KETO-EPOXYDE COMPOUNDS |
| JP2006508986A (ja) | 2002-11-20 | 2006-03-16 | エルラント ゲネ セラペウチクス エルエルシー | ヒストンデアセチラーゼ阻害剤による肺細胞の治療方法 |
| US6683092B1 (en) | 2003-04-09 | 2004-01-27 | Allergan, Inc. | [3-(c5-14alkyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-3-oxo-propenyl]-phenyl and [3-(c5-14alkyl-2-oxo-1,2,3,4- tetrahydro-quinolin-6-yl)-3-oxo-propenyl]-heteroaryl derivatives having anti-tumor activity |
| US6734193B1 (en) | 2003-06-03 | 2004-05-11 | Allergan, Inc. | (1,2,3,4-tetrahydroquinolin-8-yl)-heptatrienoic acid derivatives having serum glucose reducing activity |
| US6936636B2 (en) * | 2003-06-26 | 2005-08-30 | Allergan, Inc. | 5-[phenyl-tetrahydronaphthalene-2-yl dihydronaphthalen-2-yl and heteroaryl-cyclopropyl]-pentadienoic acid derivatives having serum glucose reducing activity |
| US6887896B1 (en) | 2003-10-29 | 2005-05-03 | Allergan, Inc. | 7-[(7-Alkoxy)-chrom-3-en-6-yl]-heptatrienoic acid and 7-[(3-alkoxy)-5,6-dihydronaphthalen-2-yl]-heptatrienoic acid derivatives having serum glucose reducing activity |
| LT1937244T (lt) | 2005-09-30 | 2018-11-12 | Io Therapeutics, Llc | Vėžio gydymas specifiniais rxr agonistais |
| US20070185055A1 (en) * | 2006-02-06 | 2007-08-09 | Guang Liang Jiang | Method for treating cachexia with retinoid ligands |
| CN110151745A (zh) | 2011-12-13 | 2019-08-23 | Io治疗公司 | 使用rxr激动剂的自身免疫紊乱的治疗 |
| US10653650B2 (en) | 2011-12-13 | 2020-05-19 | Io Therapeutics, Inc. | Treatment of diseases by concurrently eliciting remyelination effects and immunomodulatory effects using selective RXR agonists |
| JP6492432B2 (ja) * | 2013-07-09 | 2019-04-03 | 東ソー株式会社 | アダマンチル基を有する環状アジン化合物、その製造方法、及びそれを構成成分とする有機電界発光素子 |
| KR102149321B1 (ko) | 2015-10-31 | 2020-08-28 | 아이오 테라퓨틱스, 인크. | Rxr 아고니스트와 갑상선 호르몬의 조합을 사용한 신경계 질환의 치료 |
| NZ745704A (en) | 2016-03-10 | 2019-04-26 | Io Therapeutics Inc | Treatment of muscular disorders with combinations of rxr agonists and thyroid hormones |
| KR102549273B1 (ko) | 2016-03-10 | 2023-06-28 | 아이오 테라퓨틱스, 인크. | Rxr 작용제 및 갑상선 호르몬의 조합을 사용한 자가면역 질환의 치료 |
| EP3684348A4 (en) | 2017-09-20 | 2021-08-18 | IO Therapeutics, Inc. | TREATMENT OF DISEASES WITH ETERS FROM SELECTIVE RXR AGONISTS |
| KR102715396B1 (ko) * | 2017-11-17 | 2024-10-08 | 아이오 테라퓨틱스, 인크. | 레티노이드 x 수용체 특이적 레티노이드의 제조를 위한 화합물 및 합성 방법 |
| US10966950B2 (en) | 2019-06-11 | 2021-04-06 | Io Therapeutics, Inc. | Use of an RXR agonist in treating HER2+ cancers |
| EP4444287A4 (en) | 2021-12-07 | 2025-05-28 | Io Therapeutics, Inc. | USE OF AN RXR AGONIST AND TAXANES FOR THE TREATMENT OF HER2+ CANCER |
| KR20240115316A (ko) | 2021-12-07 | 2024-07-25 | 아이오 테라퓨틱스, 인크. | 약물 내성 her2+ 암 치료에서의 rxr 작용제의 용도 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8826760D0 (en) * | 1988-11-16 | 1988-12-21 | Wellcome Found | Pesticides |
| DE617614T1 (de) * | 1991-12-18 | 1995-06-08 | Baylor College Of Medicine, Houston, Tex. | Mitteln zur modulierung von verfahren durch retinoid rezeptoren und dafür nützliche verbindungen. |
| DE69333894D1 (de) * | 1992-04-22 | 2005-12-01 | Ligand Pharm Inc | Verbindungen mit Retinoid x rezeptorselektivität |
| ES2129115T3 (es) * | 1993-01-11 | 1999-06-01 | Ligand Pharm Inc | Compuestos que tienen actividad selectiva para los receptores de retinoides x, y medios para la modulacion de procesos mediados por receptores de retinoides x. |
| US5455265A (en) * | 1993-02-11 | 1995-10-03 | Allergan, Inc. | Method of treatment with compounds having selective agonist-like activity on RXR retinoid receptors |
| KR100363545B1 (ko) * | 1994-08-10 | 2003-02-19 | 에프. 호프만-라 로슈 아게 | 레틴산x-수용체리간드 |
| IL116259A (en) * | 1994-12-19 | 2000-07-16 | American Cyanamid Co | Analogs of 9-cis retinoic acid and their use |
| US5648514A (en) * | 1994-12-29 | 1997-07-15 | Allergan | Substituted acetylenes having retinoid-like biological activity |
| US5543534A (en) * | 1994-12-29 | 1996-08-06 | Allergan | Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group and with an aryl or heteroaryl groups having retinoid-like biological activity |
| US5675033A (en) * | 1995-06-06 | 1997-10-07 | Allergan | 2,4-pentadienoic acid derivatives having retinoid-like biological activity |
| US5776699A (en) * | 1995-09-01 | 1998-07-07 | Allergan, Inc. | Method of identifying negative hormone and/or antagonist activities |
| AU726450B2 (en) * | 1995-10-06 | 2000-11-09 | Ligand Pharmaceuticals Incorporated | Dimer-selective RXR modulators and methods for their use |
| US5723666A (en) * | 1996-06-21 | 1998-03-03 | Allergan | Oxime substituted tetrahydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity |
| US5728846A (en) * | 1996-12-12 | 1998-03-17 | Allergan | Benzo 1,2-g!-chrom-3-ene and benzo 1,2-g!-thiochrom-3-ene derivatives |
| CN1337931A (zh) * | 1999-03-08 | 2002-02-27 | 巴斯利尔药物股份公司 | 类维生素a拮抗剂及其用途 |
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1998
- 1998-10-01 US US09/164,950 patent/US6147224A/en not_active Expired - Fee Related
-
1999
- 1999-09-20 NZ NZ510528A patent/NZ510528A/xx unknown
- 1999-09-20 CA CA002346034A patent/CA2346034A1/en not_active Abandoned
- 1999-09-20 AT AT99970078T patent/ATE254593T1/de not_active IP Right Cessation
- 1999-09-20 DE DE69912973T patent/DE69912973T2/de not_active Expired - Fee Related
- 1999-09-20 JP JP2000574489A patent/JP2002526516A/ja active Pending
- 1999-09-20 WO PCT/US1999/021712 patent/WO2000020370A1/en not_active Ceased
- 1999-09-20 AU AU60513/99A patent/AU757932B2/en not_active Ceased
- 1999-09-20 EP EP99970078A patent/EP1117628B1/en not_active Expired - Lifetime
- 1999-09-20 ES ES99970078T patent/ES2207339T3/es not_active Expired - Lifetime
- 1999-09-20 KR KR1020017004018A patent/KR20010075457A/ko not_active Abandoned
- 1999-09-20 EP EP03025774A patent/EP1388534A3/en not_active Withdrawn
- 1999-09-20 BR BR9914256-2A patent/BR9914256A/pt not_active Application Discontinuation
- 1999-09-20 CN CN99813787A patent/CN1328538A/zh active Pending
- 1999-10-01 AR ARP990104996A patent/AR020691A1/es not_active Application Discontinuation
- 1999-10-12 TW TW088116960A patent/TW580494B/zh not_active IP Right Cessation
-
2001
- 2001-03-30 ZA ZA200102635A patent/ZA200102635B/en unknown
-
2006
- 2006-09-20 KR KR1020060091029A patent/KR20060118367A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| NZ510528A (en) | 2003-04-29 |
| EP1117628A1 (en) | 2001-07-25 |
| EP1117628B1 (en) | 2003-11-19 |
| KR20060118367A (ko) | 2006-11-23 |
| EP1388534A3 (en) | 2004-02-25 |
| JP2002526516A (ja) | 2002-08-20 |
| DE69912973T2 (de) | 2004-07-22 |
| EP1388534A2 (en) | 2004-02-11 |
| AR020691A1 (es) | 2002-05-22 |
| BR9914256A (pt) | 2001-07-03 |
| AU6051399A (en) | 2000-04-26 |
| ZA200102635B (en) | 2002-10-18 |
| CN1328538A (zh) | 2001-12-26 |
| KR20010075457A (ko) | 2001-08-09 |
| US6147224A (en) | 2000-11-14 |
| AU757932B2 (en) | 2003-03-13 |
| TW580494B (en) | 2004-03-21 |
| ES2207339T3 (es) | 2004-05-16 |
| DE69912973D1 (de) | 2003-12-24 |
| ATE254593T1 (de) | 2003-12-15 |
| HK1039477A1 (en) | 2002-04-26 |
| WO2000020370A1 (en) | 2000-04-13 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |