SK3912000A3 - Tetrahydrofuran phosphate- and hydroxy esters, as prodrugs for the corresponding antifungal agent - Google Patents
Tetrahydrofuran phosphate- and hydroxy esters, as prodrugs for the corresponding antifungal agent Download PDFInfo
- Publication number
- SK3912000A3 SK3912000A3 SK391-2000A SK3912000A SK3912000A3 SK 3912000 A3 SK3912000 A3 SK 3912000A3 SK 3912000 A SK3912000 A SK 3912000A SK 3912000 A3 SK3912000 A3 SK 3912000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- formula
- tetrahydrofuran
- compounds
- antifungal
- Prior art date
Links
- 229940121375 antifungal agent Drugs 0.000 title description 19
- 239000003429 antifungal agent Substances 0.000 title description 7
- 239000000651 prodrug Substances 0.000 title description 2
- 229940002612 prodrug Drugs 0.000 title description 2
- PSMHETLGQXNXPJ-UHFFFAOYSA-N OOP(=O)(O)O.O1CCCC1 Chemical class OOP(=O)(O)O.O1CCCC1 PSMHETLGQXNXPJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 6
- 208000031888 Mycoses Diseases 0.000 claims abstract description 6
- 230000000843 anti-fungal effect Effects 0.000 claims description 22
- 238000001990 intravenous administration Methods 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 5
- 238000001802 infusion Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229910018828 PO3H2 Inorganic materials 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 16
- -1 tetrahydrofuran compound Chemical class 0.000 description 16
- 230000037396 body weight Effects 0.000 description 15
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- 239000000243 solution Substances 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
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- 239000007787 solid Substances 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 8
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- 150000007530 organic bases Chemical class 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- HFGZFHCWKKQGIS-NOZJJQNGSA-N (2r,3r)-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C([C@@](O)([C@@H](C)S(C)(=O)=O)C=1C(=CC(F)=CC=1)F)N1C=NC=N1 HFGZFHCWKKQGIS-NOZJJQNGSA-N 0.000 description 2
- CXEFZVVLTJQWBF-UHFFFAOYSA-N 4-phenylmethoxybutanoic acid Chemical compound OC(=O)CCCOCC1=CC=CC=C1 CXEFZVVLTJQWBF-UHFFFAOYSA-N 0.000 description 2
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- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 244000052637 human pathogen Species 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 229960004130 itraconazole Drugs 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- SGECHWQKWQJBAO-UHFFFAOYSA-N n-bis(phenylmethoxy)phosphoryl-n-propan-2-ylpropan-2-amine Chemical compound C=1C=CC=CC=1COP(=O)(N(C(C)C)C(C)C)OCC1=CC=CC=C1 SGECHWQKWQJBAO-UHFFFAOYSA-N 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229960005141 piperazine Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- IWOLVLSIZCEOHM-UHFFFAOYSA-M silver;dibenzyl phosphate Chemical compound [Ag+].C=1C=CC=CC=1COP(=O)([O-])OCC1=CC=CC=C1 IWOLVLSIZCEOHM-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- WHGYBXFWUBPSRW-FEYSZYNQSA-N β-dextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)C(O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FEYSZYNQSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93782797A | 1997-09-25 | 1997-09-25 | |
| PCT/US1998/018508 WO1999015522A1 (en) | 1997-09-25 | 1998-09-22 | Tetrahydrofuran phosphate- and hydroxy esters, as prodrugs for the corresponding antifungal agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK3912000A3 true SK3912000A3 (en) | 2000-08-14 |
Family
ID=25470461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK391-2000A SK3912000A3 (en) | 1997-09-25 | 1998-09-22 | Tetrahydrofuran phosphate- and hydroxy esters, as prodrugs for the corresponding antifungal agent |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP1027349B1 (es) |
| JP (1) | JP3473949B2 (es) |
| KR (1) | KR20010024297A (es) |
| CN (1) | CN1125066C (es) |
| AR (1) | AR015458A1 (es) |
| AT (1) | ATE286502T1 (es) |
| AU (1) | AU1698199A (es) |
| BR (1) | BR9812671A (es) |
| CA (1) | CA2304624C (es) |
| CO (1) | CO5011088A1 (es) |
| DE (1) | DE69828524T2 (es) |
| ES (1) | ES2232974T3 (es) |
| HK (1) | HK1025960A1 (es) |
| HU (1) | HUP0004616A3 (es) |
| ID (1) | ID28294A (es) |
| IL (1) | IL134469A0 (es) |
| MY (1) | MY133775A (es) |
| NO (1) | NO20001557L (es) |
| NZ (1) | NZ502709A (es) |
| PE (1) | PE120799A1 (es) |
| PL (1) | PL339488A1 (es) |
| PT (1) | PT1027349E (es) |
| SK (1) | SK3912000A3 (es) |
| TR (1) | TR200000753T2 (es) |
| WO (1) | WO1999015522A1 (es) |
| ZA (1) | ZA988688B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1915500A (en) | 1998-11-20 | 2000-06-13 | Bristol-Myers Squibb Company | Water soluble prodrugs of azole compounds |
| CN102906087B (zh) * | 2010-05-19 | 2016-03-23 | 桑多斯股份公司 | 制备手性三唑酮的方法 |
| CN111138421A (zh) * | 2019-12-26 | 2020-05-12 | 上海英诺富成生物科技有限公司 | 抗真菌水溶性化合物及其制备方法与应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693626A (en) * | 1993-12-21 | 1997-12-02 | Schering Corporation | Tetrahydrofuran antifungals |
| ATE204875T1 (de) * | 1993-12-21 | 2001-09-15 | Schering Corp | Fungizide tetrahydrofurane |
-
1998
- 1998-09-22 KR KR1020007003196A patent/KR20010024297A/ko not_active Application Discontinuation
- 1998-09-22 CA CA002304624A patent/CA2304624C/en not_active Expired - Fee Related
- 1998-09-22 IL IL13446998A patent/IL134469A0/xx unknown
- 1998-09-22 EP EP98961721A patent/EP1027349B1/en not_active Expired - Lifetime
- 1998-09-22 JP JP2000512827A patent/JP3473949B2/ja not_active Expired - Fee Related
- 1998-09-22 TR TR2000/00753T patent/TR200000753T2/xx unknown
- 1998-09-22 DE DE69828524T patent/DE69828524T2/de not_active Expired - Lifetime
- 1998-09-22 MY MYPI98004343A patent/MY133775A/en unknown
- 1998-09-22 PE PE1998000905A patent/PE120799A1/es not_active Application Discontinuation
- 1998-09-22 ID IDW20000551A patent/ID28294A/id unknown
- 1998-09-22 WO PCT/US1998/018508 patent/WO1999015522A1/en not_active Application Discontinuation
- 1998-09-22 ZA ZA988688A patent/ZA988688B/xx unknown
- 1998-09-22 HU HU0004616A patent/HUP0004616A3/hu unknown
- 1998-09-22 PT PT98961721T patent/PT1027349E/pt unknown
- 1998-09-22 ES ES98961721T patent/ES2232974T3/es not_active Expired - Lifetime
- 1998-09-22 AU AU16981/99A patent/AU1698199A/en not_active Abandoned
- 1998-09-22 PL PL98339488A patent/PL339488A1/xx unknown
- 1998-09-22 NZ NZ502709A patent/NZ502709A/en unknown
- 1998-09-22 AT AT98961721T patent/ATE286502T1/de not_active IP Right Cessation
- 1998-09-22 SK SK391-2000A patent/SK3912000A3/sk unknown
- 1998-09-22 BR BR9812671-7A patent/BR9812671A/pt not_active IP Right Cessation
- 1998-09-22 CN CN98809550A patent/CN1125066C/zh not_active Expired - Fee Related
- 1998-09-22 AR ARP980104741A patent/AR015458A1/es unknown
- 1998-09-23 CO CO98055163A patent/CO5011088A1/es unknown
-
2000
- 2000-03-24 NO NO20001557A patent/NO20001557L/no not_active Application Discontinuation
- 2000-08-17 HK HK00105167A patent/HK1025960A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL134469A0 (en) | 2001-04-30 |
| DE69828524T2 (de) | 2005-12-29 |
| EP1027349B1 (en) | 2005-01-05 |
| MY133775A (en) | 2007-11-30 |
| EP1027349A1 (en) | 2000-08-16 |
| BR9812671A (pt) | 2000-08-22 |
| HK1025960A1 (en) | 2000-12-01 |
| PT1027349E (pt) | 2005-05-31 |
| ID28294A (id) | 2001-05-10 |
| AU1698199A (en) | 1999-04-12 |
| CA2304624C (en) | 2007-06-19 |
| TR200000753T2 (tr) | 2001-01-22 |
| DE69828524D1 (de) | 2005-02-10 |
| CN1271356A (zh) | 2000-10-25 |
| ZA988688B (en) | 1999-03-23 |
| KR20010024297A (ko) | 2001-03-26 |
| WO1999015522A1 (en) | 1999-04-01 |
| ES2232974T3 (es) | 2005-06-01 |
| CN1125066C (zh) | 2003-10-22 |
| JP2001517665A (ja) | 2001-10-09 |
| NZ502709A (en) | 2001-11-30 |
| AR015458A1 (es) | 2001-05-02 |
| HUP0004616A3 (en) | 2002-04-29 |
| CA2304624A1 (en) | 1999-04-01 |
| PE120799A1 (es) | 1999-12-01 |
| CO5011088A1 (es) | 2001-02-28 |
| ATE286502T1 (de) | 2005-01-15 |
| PL339488A1 (en) | 2000-12-18 |
| HUP0004616A2 (hu) | 2002-03-28 |
| NO20001557D0 (no) | 2000-03-24 |
| JP3473949B2 (ja) | 2003-12-08 |
| NO20001557L (no) | 2000-03-24 |
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