AR040412A1 - Derivados de sulfamato sustituido como anticonvulsivo - Google Patents
Derivados de sulfamato sustituido como anticonvulsivoInfo
- Publication number
- AR040412A1 AR040412A1 AR20030101652A ARP030101652A AR040412A1 AR 040412 A1 AR040412 A1 AR 040412A1 AR 20030101652 A AR20030101652 A AR 20030101652A AR P030101652 A ARP030101652 A AR P030101652A AR 040412 A1 AR040412 A1 AR 040412A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- aryl
- group
- aralkyl
- independently selected
- Prior art date
Links
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 title abstract 2
- 230000002082 anti-convulsion Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 46
- 125000003118 aryl group Chemical group 0.000 abstract 32
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 20
- 125000001424 substituent group Chemical group 0.000 abstract 19
- -1 hydroxy, carboxy Chemical group 0.000 abstract 15
- 125000003545 alkoxy group Chemical group 0.000 abstract 14
- 125000003282 alkyl amino group Chemical group 0.000 abstract 13
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 13
- 125000001072 heteroaryl group Chemical group 0.000 abstract 13
- 229910052736 halogen Inorganic materials 0.000 abstract 12
- 150000002367 halogens Chemical class 0.000 abstract 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 11
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 abstract 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910003849 O-Si Inorganic materials 0.000 abstract 1
- 229910003872 O—Si Inorganic materials 0.000 abstract 1
- 125000002009 alkene group Chemical group 0.000 abstract 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 1
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 abstract 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 206010015037 epilepsy Diseases 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
La presente se refiere a compuestos derivados de sulfamato substituido, procesos para su preparación y composiciones farmacéuticas que comprenden dichos derivados. Los compuestos de la presente son útiles para el tratamiento de la epilepsia. La presente se refiere en forma adicional a un proceso para la preparación de los compuestos de fórmula (4), en los cuales X, R3, R9, R5 y R6 son como se describen en la memoria. Reivindicación1: Un compuesto de la formula (1) en el cual X se selecciona de CH2 u O; R1 se selecciona del grupo formado por hidrogeno, alquilo, alquenilo, alquinilo, cicloalquilo, cicloalquil-alquilo, cicloalquenilo, arilo, aralquilo, heteroarilo, heteroaril-alquilo, heterocicloalquilo, heterocicloalquil-alquilo, alcoxicarbonilalquilo, -(alquil C2-8)-O-C(O)-(alquilo), -C(O)-R9, -C(O)-(alquil)-O-(alquilo), alcoxicarbonilo, ariloxicarbonilo, aralquiloxicarbonilo, -Si(R1)(O0-1R11)2, -SO2R12 y SEM; donde el grupo alquilo, cicloalquilo, arilo, heteroarilo o heterocicloalquilo, ya sea solo o como parte del grupo substituyente R1, está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, alquilo, alcoxi, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro o ciano; R2 se selecciona del grupo formado por hidroxi, alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo, cicloalquilalquilo, cicloalquenilo, arilo, ariloxi, aralquilo, aralquiloxi, heteroarilo, heteroaril-alquilo, heterocicloalquilo, heterocicloalquilalquilo, alcoxicarbonilalquilo, -(alquil C2-8)-O-C(O)-(alquilo), -C(O)-R9, -C(O)-(alquil)-O-(alquilo), alcoxicarbonilo, ariloxicarbonilo, aralquiloxicarbonilo, -C(O)O-Si(R17)3, -Si(R10)(O0-1R11)2, -SO2R12, -P(=O)(R13)2 y SEM; donde el grupo alquilo, cicloalquilo, arilo, aralquilo, heteroaril o heterocicloalquilo, ya sea solo o como parte del grupo substituyente R2, está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, alquilo, alcoxi, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro o ciano; donde cada R9 se selecciona en forma independiente de alquilo, arilo, aralquilo o heteroarilo; donde el grupo alquilo, arilo o heteroarilo, ya sea solo o como parte del grupo substituyente R9, está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, alquilo, alcoxi, alcoxicarbonilo, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro o ciano; donde cada R10 se selecciona en forma independiente de hidrogeno, alquilo, arilo o aralquilo; donde el grupo alquilo o arilo, ya sea solo o como parte del grupo substituyente R10, está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, alquilo, alcoxi, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro o ciano; donde cada R11 se selecciona en forma independiente de alquilo, arilo o aralquilo; donde el grupo alquilo o arilo, ya sea solo o como parte del grupo substituyente R11, está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, alquilo, alcoxi, alcoxicarbonilo, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro o ciano; donde cada R12 se selecciona en forma independiente de amino, alquilamino, dialquilamino, alquilo, arilo, aralquilo o heteroarilo; donde el grupo alquilo, arilo o heteroarilo, ya sea solo o como parte del grupo substituyente R12, está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de alquilo, halógeno, trifluorometilo, trifluorometoxi, alquilo, alcoxi, nitro, amino, alquilamino, dialquilamino, alquilcarbonilamino, arilcarbonilamino, aralquilcarbonilamino, arilo, heteroarilo, bencensulfonilo o fenoxi; donde el grupo fenoxi está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, alquilo, alcoxi o nitro; donde cada R13 se selecciona en forma independiente de alquilo, alcoxi, arilo, ariloxi, aralquilo o aralquiloxi; donde el grupo alquilo o arilo, ya sea solo o como parte del grupo substituyente R13, está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, alquilo, alcoxi, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro o ciano; donde cada R17 se selecciona en forma independiente de alquilo, arilo o aralquilo; donde el grupo alquilo o arilo, ya sea solo o como parte del grupo substituyente R17, está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, alquilo, alcoxi, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro o ciano; en forma alternativa, R1 y R2 se toman junto al átomo de N al cual están unidos para formar un grupo heteroarilo o heterocicloalquilo; donde el grupo heteroarilo o heterocicloalquilo está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, oxo, alquilo, alcoxi, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro, ciano, -C(=NH)-amino, -C(=NH)alquilamino o -C(=NH)-dialquilamino; donde el substituyente arilo está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, alquilo, alcoxi, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro, ciano, -C (=NH)-amino, C(=NH)-alquilamino o -C(=NH)-dialquilamino; donde el grupo -C(=NH)-amino, -C(=NH)-alquilamino o -C-(=NH)-dialquilamino está unido a un átomo de nitrógeno o carbono en el arilo, heteroarilo o heterocicloalquilo; y donde no más de un grupo -C(=NH)-amino, -C(=NH)-alquilamino o -C(=NH)-dialquilamino está unido al arilo, heteroarilo o heterocicloalquilo; en forma alternativa, R1 y R2 se toman junto al átomo de N al cual están unidos para formar -N=C(R14)2; donde cada R14 se selecciona en forma independiente de hidrogeno, alquilo, cicloalquilo, dialquilamino, arilo o aralquilo; donde el grupo alquilo, cicloalquilo o arilo, ya sea solo o como parte del grupo substituyente R14, está substituido en forma opcional con uno o más substituyentes seleccionados en forma independiente de halógeno, hidroxi, carboxi, alquilo, alcoxi, arilo, aralquilo, amino, alquilamino, dialquilamino, nitro o ciano; con la salvedad de que por lo menos un R14 se selecciona del grupo formado por hidrogeno y alquilo; en forma alternativa, dos grupos R14 se toman junto con el átomo de carbono al cual están unidos para formar un grupo heterocicloalquilo de la formula (2) donde R20 es alquilo inferior; R3, R4, R5 y R6 se seleccionan cada uno en forma independiente de hidrogeno o alquilo inferior y, cuando X es CH2, R5 y R6 pueden ser grupos alqueno unidos para formar un anillo de benceno y, cuando X es O, R3 y R4 y/o R5 y R6 juntos pueden ser un grupo metilendioxi de formula (3) donde R7 y R8 son iguales o diferentes y son hidrogeno, alquilo inferior o son alquilo y están unidos para formar un anillo ciclopentilo o ciclohexilo; con la salvedad de que cuando R1 es alquilo, R2 es distinto que alquilo; con la salvedad adicional de que cuando R1 es hidrogeno, R2 es distinto que alquilo, metilcarbonilo, fenilo, bencilo o carboxialquilo; con la salvedad adicional de que R1 y R2 cuando se los toma junto al átomo de N al cual están unidos es distinto que imidazolilo; con la salvedad adicional de que cuando X es O, R2 y R3 se toman juntos para formar un grupo metilendioxi de la formula (3), R4 y R5 se toman juntos para formar un grupo metilendioxi de la formula (3). donde R7 y R8 en cada caso son, cada uno, metilo, y R1 es hidrogeno entonces R2 es distinto que isopropilsulfonilo, 4-(N-bencil)-piperidinilo o 4-piridilo; o una de sus sales aceptables para uso farmacéutico.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37801702P | 2002-05-13 | 2002-05-13 | |
| US10/434,387 US7060725B2 (en) | 2002-05-13 | 2003-05-08 | Substituted sulfamate anticonvulsant derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR040412A1 true AR040412A1 (es) | 2005-04-06 |
Family
ID=29549890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AR20030101652A AR040412A1 (es) | 2002-05-13 | 2003-05-13 | Derivados de sulfamato sustituido como anticonvulsivo |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7060725B2 (es) |
| EP (1) | EP1506212A2 (es) |
| JP (1) | JP2005526852A (es) |
| CN (1) | CN1665828B (es) |
| AR (1) | AR040412A1 (es) |
| AU (1) | AU2003232112B2 (es) |
| BR (1) | BR0309964A (es) |
| CA (1) | CA2485966A1 (es) |
| HR (1) | HRP20041042A2 (es) |
| IL (1) | IL165108A0 (es) |
| MX (1) | MXPA04011232A (es) |
| NO (1) | NO20045369L (es) |
| NZ (1) | NZ537139A (es) |
| PL (1) | PL373910A1 (es) |
| RU (1) | RU2328502C2 (es) |
| TW (1) | TWI281472B (es) |
| UA (1) | UA78566C2 (es) |
| WO (1) | WO2003097656A2 (es) |
| ZA (1) | ZA200409989B (es) |
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|---|---|---|---|---|
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| US9173877B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of local pain |
| US9290486B1 (en) | 2014-11-05 | 2016-03-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy |
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| US9175008B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Prodrugs of anti-platelet agents |
| US9321716B1 (en) | 2014-11-05 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| US10208014B2 (en) | 2014-11-05 | 2019-02-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological disorders |
| US9932294B2 (en) | 2014-12-01 | 2018-04-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| WO2019188200A1 (ja) * | 2018-03-27 | 2019-10-03 | ダイキン工業株式会社 | スルファミン酸リチウムの製造方法及び新規スルファミン酸リチウム |
| CN110655542A (zh) * | 2018-06-29 | 2020-01-07 | 鲁南制药集团股份有限公司 | 一种2,3:4,5-双-O-(1-甲基亚乙基)-β-D-吡喃果糖氯磺酸酯的晶型 |
| CN114685526A (zh) * | 2020-12-25 | 2022-07-01 | 长沙博源医疗科技有限公司 | 一种托吡酯衍生物、免疫原、抗托吡酯特异性抗体及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4513006A (en) | 1983-09-26 | 1985-04-23 | Mcneil Lab., Inc. | Anticonvulsant sulfamate derivatives |
| US5273993A (en) * | 1989-06-12 | 1993-12-28 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfonyloxy radicals useful as pharmaceuticals |
| PT94305B (pt) | 1989-06-12 | 1997-02-28 | Robins Co Inc A H | Processo para a preparacao de compostos tendo um ou mais radicais aminossulfoniloxi uteis como produtos farmaceuticos |
| US5194446A (en) * | 1989-06-12 | 1993-03-16 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfaonyloxy radicals useful as pharmaceuticals |
| US5192785A (en) * | 1989-09-03 | 1993-03-09 | A. H. Robins Company, Incorporated | Sulfamates as antiglaucoma agents |
| US5025031A (en) * | 1989-11-30 | 1991-06-18 | A. H. Robins Co., Inc. | Aryl and aryloxyalkyl sulfamate esters useful as anticonvulsants |
| IL103172A (en) * | 1991-09-19 | 1997-01-10 | Mcneilab Inc | Preparation of chlorosulfate and sulfamate derivatives of 2, 3:4, 5-bis-o-(1-methylethylidene)-beta-d-fructopyranose and (1-methylcyclohexyl) methanol |
| US5242942A (en) * | 1992-04-28 | 1993-09-07 | Mcneilab, Inc. | Anticonvulsant fructopyranose cyclic sulfites and sulfates |
| JP3555032B2 (ja) | 1993-12-23 | 2004-08-18 | オーソ・フアーマシユーチカル・コーポレーシヨン | 抗痙攣性プソイドフルクトピラノーススルファメート類 |
| US5998380A (en) | 1995-10-13 | 1999-12-07 | New England Medical Center Hospitals, Inc. | Treatment of migraine |
| US5952187A (en) * | 1995-12-01 | 1999-09-14 | Oxis International, Inc. | Topiramate immunoassay |
| JP3602906B2 (ja) * | 1996-03-05 | 2004-12-15 | 富士写真フイルム株式会社 | 熱現像感光材料 |
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- 2003-05-09 RU RU2004133334/04A patent/RU2328502C2/ru active
- 2003-05-09 BR BR0309964-4A patent/BR0309964A/pt not_active IP Right Cessation
- 2003-05-09 MX MXPA04011232A patent/MXPA04011232A/es active IP Right Grant
- 2003-05-09 JP JP2004505387A patent/JP2005526852A/ja active Pending
- 2003-05-09 HR HR20041042A patent/HRP20041042A2/xx not_active Application Discontinuation
- 2003-05-09 PL PL03373910A patent/PL373910A1/xx not_active Application Discontinuation
- 2003-05-09 NZ NZ537139A patent/NZ537139A/en unknown
- 2003-05-09 CN CN038159910A patent/CN1665828B/zh not_active Expired - Fee Related
- 2003-05-09 EP EP03753013A patent/EP1506212A2/en not_active Withdrawn
- 2003-05-09 WO PCT/US2003/014796 patent/WO2003097656A2/en not_active Ceased
- 2003-05-09 CA CA002485966A patent/CA2485966A1/en not_active Abandoned
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- 2003-05-13 AR AR20030101652A patent/AR040412A1/es unknown
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- 2003-09-05 UA UA20041210256A patent/UA78566C2/uk unknown
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- 2004-12-09 ZA ZA200409989A patent/ZA200409989B/xx unknown
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2005
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| IL165108A0 (en) | 2005-12-18 |
| MXPA04011232A (es) | 2005-08-16 |
| CN1665828A (zh) | 2005-09-07 |
| CA2485966A1 (en) | 2003-11-27 |
| RU2328502C2 (ru) | 2008-07-10 |
| WO2003097656A2 (en) | 2003-11-27 |
| BR0309964A (pt) | 2005-03-01 |
| US7560459B2 (en) | 2009-07-14 |
| AU2003232112A1 (en) | 2003-12-02 |
| CN1665828B (zh) | 2012-06-27 |
| NO20045369L (no) | 2004-12-08 |
| RU2004133334A (ru) | 2005-06-10 |
| US7060725B2 (en) | 2006-06-13 |
| TWI281472B (en) | 2007-05-21 |
| ZA200409989B (en) | 2006-02-22 |
| TW200404078A (en) | 2004-03-16 |
| EP1506212A2 (en) | 2005-02-16 |
| HRP20041042A2 (hr) | 2009-04-30 |
| JP2005526852A (ja) | 2005-09-08 |
| US20060058373A1 (en) | 2006-03-16 |
| UA78566C2 (en) | 2007-04-10 |
| NZ537139A (en) | 2008-05-30 |
| US20040038911A1 (en) | 2004-02-26 |
| WO2003097656A3 (en) | 2004-06-10 |
| AU2003232112B2 (en) | 2008-12-18 |
| PL373910A1 (en) | 2005-09-19 |
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