UA75369C2 - Phenoxyphenyl alkane sulfonates, a method for the preparation thereof and medicament based thereon - Google Patents
Phenoxyphenyl alkane sulfonates, a method for the preparation thereof and medicament based thereon Download PDFInfo
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- UA75369C2 UA75369C2 UA2003043896A UA2003043896A UA75369C2 UA 75369 C2 UA75369 C2 UA 75369C2 UA 2003043896 A UA2003043896 A UA 2003043896A UA 2003043896 A UA2003043896 A UA 2003043896A UA 75369 C2 UA75369 C2 UA 75369C2
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- UA
- Ukraine
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- compounds
- compounds according
- trifluoromethyl
- salts
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- 238000000034 method Methods 0.000 title claims abstract description 47
- -1 Phenoxyphenyl alkane sulfonates Chemical class 0.000 title claims abstract description 13
- 239000003814 drug Substances 0.000 title abstract description 5
- 238000002360 preparation method Methods 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- 239000011737 fluorine Substances 0.000 claims abstract description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000003868 ammonium compounds Chemical class 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000016507 interphase Effects 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 238000012546 transfer Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 208000002193 Pain Diseases 0.000 abstract description 16
- 238000011282 treatment Methods 0.000 abstract description 12
- 230000036407 pain Effects 0.000 abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 8
- 201000010099 disease Diseases 0.000 abstract description 7
- 230000004770 neurodegeneration Effects 0.000 abstract description 6
- 208000015122 neurodegenerative disease Diseases 0.000 abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 150000003871 sulfonates Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000126 substance Substances 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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- 241000700159 Rattus Species 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 230000014759 maintenance of location Effects 0.000 description 13
- 238000001819 mass spectrum Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 7
- 229960003742 phenol Drugs 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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- C07C309/01—Sulfonic acids
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- C07C309/20—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C309/22—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
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- Rheumatology (AREA)
- Anesthesiology (AREA)
- Psychology (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10047486A DE10047486A1 (de) | 2000-09-26 | 2000-09-26 | Phenoxyphenyl Alkansulfonate |
PCT/EP2001/010564 WO2002026702A1 (fr) | 2000-09-26 | 2001-09-13 | Sulfonates d'alcane de phenoxyphenyle |
Publications (1)
Publication Number | Publication Date |
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UA75369C2 true UA75369C2 (en) | 2006-04-17 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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UA2003043896A UA75369C2 (en) | 2000-09-26 | 2001-09-13 | Phenoxyphenyl alkane sulfonates, a method for the preparation thereof and medicament based thereon |
Country Status (34)
Country | Link |
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US (2) | US6756409B2 (fr) |
EP (1) | EP1334086B1 (fr) |
JP (1) | JP2004509946A (fr) |
KR (1) | KR20030039372A (fr) |
CN (1) | CN1476427A (fr) |
AR (1) | AR033575A1 (fr) |
AT (1) | ATE292621T1 (fr) |
AU (2) | AU2054702A (fr) |
BG (1) | BG107634A (fr) |
BR (1) | BR0114182A (fr) |
CA (1) | CA2423171A1 (fr) |
DE (2) | DE10047486A1 (fr) |
EE (1) | EE200300117A (fr) |
ES (1) | ES2240543T3 (fr) |
GT (1) | GT200100193A (fr) |
HN (1) | HN2001000214A (fr) |
HR (1) | HRP20030326A2 (fr) |
HU (1) | HUP0302258A3 (fr) |
IL (1) | IL154968A0 (fr) |
MA (1) | MA26053A1 (fr) |
MX (1) | MXPA03002546A (fr) |
NO (1) | NO20031357L (fr) |
NZ (1) | NZ524886A (fr) |
PE (1) | PE20020408A1 (fr) |
PL (1) | PL361015A1 (fr) |
PT (1) | PT1334086E (fr) |
RU (1) | RU2278853C2 (fr) |
SI (1) | SI1334086T1 (fr) |
SK (1) | SK3442003A3 (fr) |
SV (1) | SV2002000639A (fr) |
UA (1) | UA75369C2 (fr) |
UY (1) | UY26945A1 (fr) |
WO (1) | WO2002026702A1 (fr) |
ZA (1) | ZA200302275B (fr) |
Families Citing this family (4)
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WO2003061699A1 (fr) * | 2001-12-27 | 2003-07-31 | Japan Tobacco, Inc. | Remedes pour affections allergiques |
US8772326B2 (en) | 2008-07-10 | 2014-07-08 | Anigion Biomedica Corp. | Methods and compositions of small molecule modulators of hepatocyte growth factor (scatter factor) activity |
US10709497B2 (en) * | 2017-09-22 | 2020-07-14 | Covidien Lp | Electrosurgical tissue sealing device with non-stick coating |
SG11202110406SA (en) | 2019-04-11 | 2021-10-28 | Angion Biomedica Corp | Solid forms of (e)-3-[2-(2-thienyl)vinyl]-1h-pyrazole |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
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DE216642C (fr) * | ||||
BE786644A (fr) * | 1971-07-23 | 1973-01-24 | Hoechst Ag | Derives d'acides phenoxy-4 phenoxy-alcane-carboxyliques leur preparation et les medicaments qui en contiennent |
US3914418A (en) * | 1971-09-02 | 1975-10-21 | Merck & Co Inc | Methods of controlling liver fluke infections |
GB8914660D0 (en) * | 1989-06-26 | 1989-08-16 | Fujisawa Pharmaceutical Co | Aniline derivatives,processes for production thereof and pharmaceutical compositions comprising the same |
MY117939A (en) * | 1996-07-25 | 2004-08-30 | Lg Chemical Ltd | Composition for enhancing oral hygiene |
US6090839A (en) * | 1996-12-23 | 2000-07-18 | Merck & Co., Inc. | Antidiabetic agents |
PT966436E (pt) * | 1997-02-21 | 2003-03-31 | Bayer Ag | Arilsulfonamidas e analogos e sua aplicacao para o tratamento de doencas neurodegenerativas |
US5925654A (en) * | 1997-03-12 | 1999-07-20 | G.D. Searle & Co. | LTA4 , hydrolase inhibitors |
ATE231487T1 (de) * | 1997-10-20 | 2003-02-15 | Taisho Pharmaceutical Co Ltd | 2-phenoxyanilin-derivate |
US6231875B1 (en) * | 1998-03-31 | 2001-05-15 | Johnson & Johnson Consumer Companies, Inc. | Acidified composition for topical treatment of nail and skin conditions |
NL1008795C2 (nl) * | 1998-04-02 | 1999-10-05 | Rene Werenfridus Lodewijk Vroo | Samenstelling voor het behandelen van hoeven en werkwijze voor het vervaardigen van de samenstelling. |
HN1998000027A (es) * | 1998-08-19 | 1999-06-02 | Bayer Ip Gmbh | Arilsulfonamidas y analagos |
DE19837627A1 (de) * | 1998-08-19 | 2000-02-24 | Bayer Ag | Neue Aminosäureester von Arylsulfonamiden und Analoga |
US6242422B1 (en) * | 1998-10-22 | 2001-06-05 | Idun Pharmacueticals, Inc. | (Substituted)Acyl dipeptidyl inhibitors of the ice/ced-3 family of cysteine proteases |
-
2000
- 2000-09-26 DE DE10047486A patent/DE10047486A1/de not_active Withdrawn
-
2001
- 2001-09-13 AU AU2054702A patent/AU2054702A/xx active Pending
- 2001-09-13 AU AU2002220547A patent/AU2002220547B2/en not_active Ceased
- 2001-09-13 EP EP01985700A patent/EP1334086B1/fr not_active Expired - Lifetime
- 2001-09-13 CA CA002423171A patent/CA2423171A1/fr not_active Abandoned
- 2001-09-13 AT AT01985700T patent/ATE292621T1/de not_active IP Right Cessation
- 2001-09-13 SK SK344-2003A patent/SK3442003A3/sk unknown
- 2001-09-13 KR KR10-2003-7003902A patent/KR20030039372A/ko not_active Application Discontinuation
- 2001-09-13 PT PT01985700T patent/PT1334086E/pt unknown
- 2001-09-13 MX MXPA03002546A patent/MXPA03002546A/es active IP Right Grant
- 2001-09-13 RU RU2003112454/04A patent/RU2278853C2/ru not_active IP Right Cessation
- 2001-09-13 CN CNA01819527XA patent/CN1476427A/zh active Pending
- 2001-09-13 NZ NZ524886A patent/NZ524886A/en unknown
- 2001-09-13 UA UA2003043896A patent/UA75369C2/uk unknown
- 2001-09-13 SI SI200130356T patent/SI1334086T1/xx unknown
- 2001-09-13 PL PL01361015A patent/PL361015A1/xx not_active Application Discontinuation
- 2001-09-13 JP JP2002531088A patent/JP2004509946A/ja active Pending
- 2001-09-13 BR BR0114182-1A patent/BR0114182A/pt not_active IP Right Cessation
- 2001-09-13 HU HU0302258A patent/HUP0302258A3/hu unknown
- 2001-09-13 ES ES01985700T patent/ES2240543T3/es not_active Expired - Lifetime
- 2001-09-13 EE EEP200300117A patent/EE200300117A/xx unknown
- 2001-09-13 DE DE50105857T patent/DE50105857D1/de not_active Expired - Fee Related
- 2001-09-13 WO PCT/EP2001/010564 patent/WO2002026702A1/fr active IP Right Grant
- 2001-09-13 IL IL15496801A patent/IL154968A0/xx unknown
- 2001-09-24 AR ARP010104486A patent/AR033575A1/es not_active Application Discontinuation
- 2001-09-24 GT GT200100193A patent/GT200100193A/es unknown
- 2001-09-24 UY UY26945A patent/UY26945A1/es not_active Application Discontinuation
- 2001-09-25 PE PE2001000958A patent/PE20020408A1/es not_active Application Discontinuation
- 2001-09-25 SV SV2001000639A patent/SV2002000639A/es unknown
- 2001-09-25 HN HN2001000214A patent/HN2001000214A/es unknown
- 2001-09-26 US US09/965,708 patent/US6756409B2/en not_active Expired - Fee Related
-
2003
- 2003-03-13 BG BG107634A patent/BG107634A/bg unknown
- 2003-03-24 ZA ZA200302275A patent/ZA200302275B/en unknown
- 2003-03-25 MA MA27075A patent/MA26053A1/fr unknown
- 2003-03-25 NO NO20031357A patent/NO20031357L/no not_active Application Discontinuation
- 2003-04-25 HR HR20030326A patent/HRP20030326A2/hr not_active Application Discontinuation
-
2004
- 2004-05-20 US US10/850,507 patent/US20040214886A1/en not_active Abandoned
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