HRP20040395A2 - Novel mandelate salts of substituted tetracyclic tetrahydrofuran derivatives - Google Patents
Novel mandelate salts of substituted tetracyclic tetrahydrofuran derivatives Download PDFInfo
- Publication number
- HRP20040395A2 HRP20040395A2 HR20040395A HRP20040395A HRP20040395A2 HR P20040395 A2 HRP20040395 A2 HR P20040395A2 HR 20040395 A HR20040395 A HR 20040395A HR P20040395 A HRP20040395 A HR P20040395A HR P20040395 A2 HRP20040395 A2 HR P20040395A2
- Authority
- HR
- Croatia
- Prior art keywords
- mandelic acid
- salt
- dibenzo
- furan
- cyclohepta
- Prior art date
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title description 12
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical class [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 title description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 44
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 28
- 229960002510 mandelic acid Drugs 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 23
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- 239000001257 hydrogen Substances 0.000 claims description 18
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- 239000000203 mixture Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
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- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
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- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
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- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 208000019906 panic disease Diseases 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
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- 239000008159 sesame oil Substances 0.000 description 1
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- 208000012201 sexual and gender identity disease Diseases 0.000 description 1
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- 238000005055 short column chromatography Methods 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01204465 | 2001-11-09 | ||
| PCT/EP2002/011136 WO2003040122A1 (en) | 2001-11-09 | 2002-11-08 | Novel mandelate salts of substituted tetracyclic tetrahydrofuran derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040395A2 true HRP20040395A2 (en) | 2005-04-30 |
Family
ID=8181272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040395A HRP20040395A2 (en) | 2001-11-09 | 2004-05-05 | Novel mandelate salts of substituted tetracyclic tetrahydrofuran derivatives |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7317115B2 (pt) |
| EP (1) | EP1446397B1 (pt) |
| JP (1) | JP2005508988A (pt) |
| KR (1) | KR100962325B1 (pt) |
| CN (1) | CN1582282B (pt) |
| AR (1) | AR037285A1 (pt) |
| AT (1) | ATE299138T1 (pt) |
| AU (1) | AU2002349327B2 (pt) |
| BR (1) | BR0212770A (pt) |
| CA (1) | CA2465043C (pt) |
| DE (1) | DE60204982T2 (pt) |
| EA (1) | EA006980B1 (pt) |
| ES (1) | ES2244818T3 (pt) |
| HR (1) | HRP20040395A2 (pt) |
| HU (1) | HUP0402224A3 (pt) |
| IL (2) | IL161866A0 (pt) |
| MX (1) | MXPA04004365A (pt) |
| MY (1) | MY128237A (pt) |
| NO (1) | NO328548B1 (pt) |
| NZ (1) | NZ531739A (pt) |
| PL (1) | PL368456A1 (pt) |
| TW (1) | TW200407117A (pt) |
| UA (1) | UA79248C2 (pt) |
| WO (1) | WO2003040122A1 (pt) |
| ZA (1) | ZA200403454B (pt) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6998494B2 (en) * | 2001-12-07 | 2006-02-14 | Janssen Pharmaceutica N.V. | Preparation of trans-fused 3,3a,8,12b-tetrahydro-2h-dibenzo[3,4:6,7]cyclohepta[1,2-b]furan derivatives |
| WO2005013969A1 (en) * | 2003-07-15 | 2005-02-17 | Janssen Pharmaceutica N.V. | Antipsychotic agent with socializing properties |
| AU2005313325C1 (en) | 2004-12-07 | 2011-11-10 | Janssen Pharmaceutica N.V. | Substituted tetracyclic tetrahydrofuran, pyrrolidine and tetrahydrothiophene derivatives |
| CN101107254B (zh) | 2005-01-27 | 2010-12-08 | 詹森药业有限公司 | 在中枢神经系统病症的治疗中作为5ht2抑制剂的杂环四环四氢呋喃衍生物 |
| WO2006134163A2 (en) | 2005-06-17 | 2006-12-21 | Janssen Pharmaceutica N.V. | Novel tetracyclic tetrahydrofuran derivatives containing a cyclic amine side chain |
| US8507040B2 (en) | 2008-05-08 | 2013-08-13 | Air Products And Chemicals, Inc. | Binary and ternary metal chalcogenide materials and method of making and using same |
| US8765223B2 (en) * | 2008-05-08 | 2014-07-01 | Air Products And Chemicals, Inc. | Binary and ternary metal chalcogenide materials and method of making and using same |
| US8962675B1 (en) * | 2013-09-12 | 2015-02-24 | Abbvie Inc. | Atrasentan mandelate salts |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3644462A1 (de) | 1986-12-24 | 1988-07-07 | Basf Ag | Verfahren zur herstellung von 5h-dibenzo(a,d)cyclohepten-5-onen |
| JP2656720B2 (ja) * | 1992-12-09 | 1997-09-24 | 武田薬品工業株式会社 | 光学活性アミノクマラン誘導体 |
| AU1945495A (en) * | 1994-03-16 | 1995-10-03 | Novo Nordisk A/S | Acid addition salts of 2,3,4,5-tetrahydro-1h-3-benzazepine compounds |
| JP3199751B2 (ja) * | 1996-04-12 | 2001-08-20 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 置換された四環式テトラヒドロフラン誘導体 |
| EE03902B1 (et) | 1996-05-20 | 2002-12-16 | Janssen Pharmaceutica N.V. | Osakesed, nende valmistamismeetod ja kasutamine, farmatseutiline doseerimisvorm ja selle valmistamismeetod, tahke dispersioon ning farmatseutiline pakend |
| UA52778C2 (uk) * | 1997-10-10 | 2003-01-15 | Янссен Фармацевтика Н.В. | Галогенозаміщені тетрациклічні похідні тетрагідрофурану, спосіб їх отримання та композиція на їх основі |
| US6281247B1 (en) * | 1998-03-03 | 2001-08-28 | Novo Nordisk A/S | Salt forms of (2E)-5-amino-5-methylhex-2-enoic acid N-methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)amide |
| HUP9904624A2 (hu) * | 1999-12-17 | 2002-01-28 | Sanofi-Synthelabo | Szacharinszármazékok, eljárás előállításukra, az ezeket tartalmazó gyógyszerkészítmények és intermedierjeik |
| EP1186303A3 (en) * | 2000-09-06 | 2003-12-10 | Pfizer Products Inc. | Pharmaceutical combinations, for the treatment of stroke and traumatic brain injury, containing a neutrophil inhibiting factor and an selective NMDA-NR2B receptor antagonist |
-
2002
- 2002-08-11 UA UA20040604168A patent/UA79248C2/uk unknown
- 2002-11-07 MY MYPI20024166A patent/MY128237A/en unknown
- 2002-11-08 NZ NZ531739A patent/NZ531739A/en not_active IP Right Cessation
- 2002-11-08 AR ARP020104298A patent/AR037285A1/es unknown
- 2002-11-08 AU AU2002349327A patent/AU2002349327B2/en not_active Ceased
- 2002-11-08 MX MXPA04004365A patent/MXPA04004365A/es active IP Right Grant
- 2002-11-08 TW TW091132840A patent/TW200407117A/zh unknown
- 2002-11-08 US US10/491,799 patent/US7317115B2/en not_active Expired - Fee Related
- 2002-11-08 CA CA2465043A patent/CA2465043C/en not_active Expired - Fee Related
- 2002-11-08 ES ES02781214T patent/ES2244818T3/es not_active Expired - Lifetime
- 2002-11-08 KR KR1020047002379A patent/KR100962325B1/ko not_active IP Right Cessation
- 2002-11-08 AT AT02781214T patent/ATE299138T1/de not_active IP Right Cessation
- 2002-11-08 PL PL02368456A patent/PL368456A1/xx unknown
- 2002-11-08 DE DE60204982T patent/DE60204982T2/de not_active Expired - Lifetime
- 2002-11-08 EA EA200400656A patent/EA006980B1/ru not_active IP Right Cessation
- 2002-11-08 CN CN02821918XA patent/CN1582282B/zh not_active Expired - Fee Related
- 2002-11-08 EP EP02781214A patent/EP1446397B1/en not_active Expired - Lifetime
- 2002-11-08 HU HU0402224A patent/HUP0402224A3/hu unknown
- 2002-11-08 WO PCT/EP2002/011136 patent/WO2003040122A1/en active IP Right Grant
- 2002-11-08 BR BR0212770-9A patent/BR0212770A/pt not_active IP Right Cessation
- 2002-11-08 IL IL16186602A patent/IL161866A0/xx unknown
- 2002-11-08 JP JP2003542168A patent/JP2005508988A/ja active Pending
-
2004
- 2004-05-05 HR HR20040395A patent/HRP20040395A2/hr not_active Application Discontinuation
- 2004-05-05 NO NO20041848A patent/NO328548B1/no not_active IP Right Cessation
- 2004-05-06 ZA ZA200403454A patent/ZA200403454B/en unknown
- 2004-05-06 IL IL161866A patent/IL161866A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2465043A1 (en) | 2003-05-15 |
| EA006980B1 (ru) | 2006-06-30 |
| EP1446397B1 (en) | 2005-07-06 |
| TW200407117A (en) | 2004-05-16 |
| AR037285A1 (es) | 2004-11-03 |
| EP1446397A1 (en) | 2004-08-18 |
| IL161866A (en) | 2010-04-29 |
| KR20050044310A (ko) | 2005-05-12 |
| DE60204982T2 (de) | 2006-04-27 |
| ES2244818T3 (es) | 2005-12-16 |
| HUP0402224A2 (hu) | 2005-02-28 |
| AU2002349327B2 (en) | 2008-10-23 |
| PL368456A1 (en) | 2005-03-21 |
| CN1582282A (zh) | 2005-02-16 |
| KR100962325B1 (ko) | 2010-06-11 |
| US7317115B2 (en) | 2008-01-08 |
| HUP0402224A3 (en) | 2007-05-29 |
| US20050085533A1 (en) | 2005-04-21 |
| DE60204982D1 (de) | 2005-08-11 |
| NO20041848L (no) | 2004-05-05 |
| EA200400656A1 (ru) | 2004-10-28 |
| MXPA04004365A (es) | 2004-08-11 |
| NZ531739A (en) | 2005-02-25 |
| IL161866A0 (en) | 2005-11-20 |
| UA79248C2 (en) | 2007-06-11 |
| CN1582282B (zh) | 2012-06-06 |
| MY128237A (en) | 2007-01-31 |
| ZA200403454B (en) | 2005-08-31 |
| JP2005508988A (ja) | 2005-04-07 |
| WO2003040122A1 (en) | 2003-05-15 |
| ATE299138T1 (de) | 2005-07-15 |
| NO328548B1 (no) | 2010-03-15 |
| BR0212770A (pt) | 2004-10-13 |
| CA2465043C (en) | 2011-02-15 |
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