HUP0300828A2 - Process for making n-aryl-anthranilic acids and their derivatives - Google Patents
Process for making n-aryl-anthranilic acids and their derivativesInfo
- Publication number
- HUP0300828A2 HUP0300828A2 HU0300828A HUP0300828A HUP0300828A2 HU P0300828 A2 HUP0300828 A2 HU P0300828A2 HU 0300828 A HU0300828 A HU 0300828A HU P0300828 A HUP0300828 A HU P0300828A HU P0300828 A2 HUP0300828 A2 HU P0300828A2
- Authority
- HU
- Hungary
- Prior art keywords
- aryl
- general formula
- compound
- carbon atom
- derivatives
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- 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
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Abstract
A találmány tárgyát eljárás képezi ismert gyulladásgátló hatású N-aril-antranilsavak valamint ezek származékinak, így észtereinek,amidjainak és hidroxámsav-észtereinek előállítására. Az (I) általánosképletben a szubsztituensek jelentése igen sokféle, így például R1jelentése hidrogénatom, alkil-, alkoxi- vagy arilcsoport; R2, R3, R4,R5, R6, R7, R8, R9 és R10 jelentése például egymástól függetlenülválasztható halogénatom, alkil-, aril-, heterociklusos csoport,halogén-alkil-, -CN, -(O)m-(CH2)n-R11 vagy -[N(H)]m-(CH2)n-R11 csoportközül, vagy R2, R3, R4, R5, R6, R7, R8, R9 és R10 közül bármelyik kétszubsztituens, amelyek szomszédos gyűrű szénatomhoz kapcsolódnak, aszomszédos gyűrű szénatommal együtt például aril-, heterociklusos-vagy cikloalkilcsoportot képezhetnek, vagy R1 és R6 a nitrogénatommalegyütt, amelyhez R1 kapcsolódik, és például a szénatommal együtt,amelyhez R6 kapcsolódik, 5- vagy 6-tagú aromás vagy dihidroaromásgyűrűt képezhetnek, Z jelentése -COOH, -COOM, -COOR15, -C(O)N(R16)R17,-C(O)N (R18)OR19, -NO2 vagy -CN. Az (I) általános képletű vegyületettöbbféle módon állítják elő, így például (A) általános képletűvegyületet (B) általános képletű vegyülettel reagáltatnak, adottesetben egy oldószerben és 1-10 mólekvivalens bázis jelenlétében. ÓThe subject of the invention is a process for the production of known anti-inflammatory N-arylanthranilic acids and their derivatives, such as their esters, amides and hydroxamic acid esters. The meanings of the substituents in the general formula (I) are very diverse, so for example R1 means a hydrogen atom, an alkyl, alkoxy or aryl group; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are, for example, independently selectable halogen atom, alkyl-, aryl-, heterocyclic group, haloalkyl-, -CN, -(O)m-(CH2)n -R11 or -[N(H)]m-(CH2)n-R11, or any two substituents from R2, R3, R4, R5, R6, R7, R8, R9 and R10, which are attached to an adjacent ring carbon atom, adjacent ring together with a carbon atom they can form, for example, an aryl, heterocyclic or cycloalkyl group, or R1 and R6 together with the nitrogen atom to which R1 is connected and, for example, together with the carbon atom to which R6 is connected, they can form a 5- or 6-membered aromatic or dihydroaromatic ring, Z means -COOH, - COOM, -COOR15, -C(O)N(R16)R17, -C(O)N(R18)OR19, -NO2 or -CN. The compound of general formula (I) is produced in several ways, such as, for example, compound of general formula (A) is reacted with compound of general formula (B), optionally in a solvent and in the presence of 1-10 molar equivalents of base. HE
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22820600P | 2000-08-25 | 2000-08-25 | |
| PCT/US2001/022948 WO2002018319A1 (en) | 2000-08-25 | 2001-07-20 | Process for making n-aryl-anthranilic acids and their derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0300828A2 true HUP0300828A2 (en) | 2003-09-29 |
Family
ID=22856235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0300828A HUP0300828A2 (en) | 2000-08-25 | 2001-07-20 | Process for making n-aryl-anthranilic acids and their derivatives |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP1313694A1 (en) |
| JP (1) | JP2004507518A (en) |
| KR (1) | KR20030059115A (en) |
| CN (1) | CN1458921A (en) |
| AP (1) | AP2001002249A0 (en) |
| AR (1) | AR032175A1 (en) |
| AU (1) | AU2001277044A1 (en) |
| BG (1) | BG107635A (en) |
| BR (1) | BR0113520A (en) |
| CA (1) | CA2420003A1 (en) |
| CZ (1) | CZ2003477A3 (en) |
| DO (1) | DOP2001000238A (en) |
| EA (1) | EA200300187A1 (en) |
| GT (1) | GT200100174A (en) |
| HN (1) | HN2001000216A (en) |
| HU (1) | HUP0300828A2 (en) |
| IL (1) | IL154507A0 (en) |
| IS (1) | IS6724A (en) |
| MA (1) | MA26949A1 (en) |
| MX (1) | MXPA03001654A (en) |
| NO (1) | NO20030844L (en) |
| PA (1) | PA8526501A1 (en) |
| PE (1) | PE20020393A1 (en) |
| PL (1) | PL360699A1 (en) |
| SK (1) | SK2072003A3 (en) |
| SV (1) | SV2002000601A (en) |
| TN (1) | TNSN01127A1 (en) |
| UY (1) | UY26908A1 (en) |
| WO (1) | WO2002018319A1 (en) |
| YU (1) | YU14303A (en) |
| ZA (1) | ZA200301182B (en) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7235537B2 (en) | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| SG148857A1 (en) | 2002-03-13 | 2009-01-29 | Array Biopharma Inc | N3 alkylated benzimidazole derivatives as mek inhibitors |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| US7144907B2 (en) | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| EP1682495A1 (en) | 2003-10-21 | 2006-07-26 | Warner-Lambert Company LLC | Polymorphic form of n- (r)-2,3-dihydroxy-propoxy -3,4-d ifluoro-2-(2-fluoro-4-iodophenylamino)-benzamide |
| AU2004293019B2 (en) | 2003-11-19 | 2010-10-28 | Array Biopharma Inc. | Bicyclic inhibitors of MEK and methods of use thereof |
| US7732616B2 (en) | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
| US7517994B2 (en) | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| KR101223914B1 (en) | 2003-11-21 | 2013-01-18 | 어레이 바이오파마 인크. | Akt protein kinase inhibitors |
| UA89035C2 (en) * | 2003-12-03 | 2009-12-25 | Лео Фарма А/С | Hydroxamic acid esters and pharmaceutical use thereof |
| MX2007012659A (en) | 2005-04-13 | 2008-01-11 | Astex Therapeutics Ltd | Hydroxybenzamide derivatives and their use as inhibitors of hsp90. |
| TWI441637B (en) | 2005-05-18 | 2014-06-21 | Array Biopharma Inc | Heterocyclic inhibitors of mek and methods of use thereof |
| US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
| DE602007011628D1 (en) | 2006-07-06 | 2011-02-10 | Array Biopharma Inc | DIHYDROFUROPYRIMIDINES AS ACT PROTEIN KINASE INHIBITORS |
| WO2008006039A1 (en) | 2006-07-06 | 2008-01-10 | Array Biopharma Inc. | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
| MY147628A (en) | 2006-07-06 | 2012-12-31 | Array Biopharma Inc | Cyclopenta [d] pyrimidines as akt protein kinase inhibitors |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| EP2073807A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP5721949B2 (en) | 2006-10-12 | 2015-05-20 | アステックス、セラピューティックス、リミテッドＡｓｔｅｘ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | Compound drug |
| WO2008044027A2 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical compounds having hsp90 inhibitory or modulating activity |
| EP2073804B1 (en) | 2006-10-12 | 2017-09-13 | Astex Therapeutics Limited | Hydroxy-substituted benzoic acid amide compounds for use in the treatment of pain |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| CA2692506C (en) | 2007-07-05 | 2015-11-24 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| CN103396409B (en) | 2007-07-05 | 2015-03-11 | 阵列生物制药公司 | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| CA2711699A1 (en) | 2008-01-09 | 2009-07-16 | Array Biopharma Inc. | Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| EP2240455B1 (en) | 2008-01-09 | 2012-12-26 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor |
| GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| CN101985428B (en) * | 2009-07-29 | 2014-02-12 | 杭州民生药业有限公司 | O-anilino benzoic acid derivatives or pharmaceutically acceptable salts thereof as well as preparation method and application thereof |
| EP2536683A1 (en) * | 2010-02-19 | 2012-12-26 | Centre National De La Recherche Scientifique | Method for preparing chemical compounds of interest by aromatic nucleophilic substitution |
| JP2013519715A (en) * | 2010-02-19 | 2013-05-30 | センター ナショナル デ ラ リシェルシェ サイエンティフィック | Process for the preparation of desired chemical compounds by aromatic nucleophilic substitution of aromatic carboxylic acid derivatives having at least one electron withdrawing group |
| SG194048A1 (en) | 2011-04-01 | 2013-11-29 | Genentech Inc | Combinations of akt inhibitor compounds and chemotherapeutic agents, and methods of use |
| CN103841976A (en) | 2011-04-01 | 2014-06-04 | 基因泰克公司 | Combinations of AKT AND MEK inhibitor compounds, and methods of use |
| SI2909188T1 (en) * | 2012-10-12 | 2018-07-31 | Exelixis, Inc. | Novel process for making compounds for use in the treatment of cancer |
| CN112745237B (en) * | 2019-10-29 | 2023-06-20 | 中国科学院上海药物研究所 | 2-arylamine compound and preparation method and application thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3138636A (en) * | 1960-06-23 | 1964-06-23 | Parke Davis & Co | Anthranilic acid derivatives |
| US6251943B1 (en) * | 1997-02-28 | 2001-06-26 | Warner-Lambert Company | Method of treating or preventing septic shock by administering a MEK inhibitor |
| ES2274572T3 (en) * | 1997-07-01 | 2007-05-16 | Warner-Lambert Company Llc | ACID DERIVATIVES 2- (4-BROMO- OR 4-IODO-PHENYLAMINE) BENZOIC AND ITS USE AS A MEK INHIBITOR. |
| WO1999001426A1 (en) * | 1997-07-01 | 1999-01-14 | Warner-Lambert Company | 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as mek inhibitors |
| CA2348236A1 (en) * | 1999-01-13 | 2000-07-20 | Stephen Douglas Barrett | 4-arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective mek inhibitors |
| UA70995C2 (en) * | 1999-04-21 | 2004-11-15 | Ворнер-Ламберт Компані | a method for making 2-(N-phenylamino)benzoic acid |
-
2001
- 2001-07-20 PL PL36069901A patent/PL360699A1/en unknown
- 2001-07-20 CZ CZ2003477A patent/CZ2003477A3/en unknown
- 2001-07-20 CA CA002420003A patent/CA2420003A1/en not_active Abandoned
- 2001-07-20 AU AU2001277044A patent/AU2001277044A1/en not_active Abandoned
- 2001-07-20 SK SK207-2003A patent/SK2072003A3/en unknown
- 2001-07-20 JP JP2002523437A patent/JP2004507518A/en active Pending
- 2001-07-20 EA EA200300187A patent/EA200300187A1/en unknown
- 2001-07-20 AP APAP/P/2001/002249A patent/AP2001002249A0/en unknown
- 2001-07-20 WO PCT/US2001/022948 patent/WO2002018319A1/en not_active Application Discontinuation
- 2001-07-20 BR BR0113520-1A patent/BR0113520A/en not_active Application Discontinuation
- 2001-07-20 YU YU14303A patent/YU14303A/en unknown
- 2001-07-20 HU HU0300828A patent/HUP0300828A2/en unknown
- 2001-07-20 KR KR10-2003-7002675A patent/KR20030059115A/en not_active Application Discontinuation
- 2001-07-20 IL IL15450701A patent/IL154507A0/en unknown
- 2001-07-20 EP EP01954824A patent/EP1313694A1/en not_active Withdrawn
- 2001-07-20 MX MXPA03001654A patent/MXPA03001654A/en unknown
- 2001-07-20 CN CN01815869A patent/CN1458921A/en active Pending
- 2001-08-15 SV SV2001000601A patent/SV2002000601A/en not_active Application Discontinuation
- 2001-08-22 TN TNTNSN01127A patent/TNSN01127A1/en unknown
- 2001-08-23 PA PA20018526501A patent/PA8526501A1/en unknown
- 2001-08-24 GT GT200100174A patent/GT200100174A/en unknown
- 2001-08-24 AR ARP010104047A patent/AR032175A1/en unknown
- 2001-08-24 DO DO2001000238A patent/DOP2001000238A/en unknown
- 2001-08-24 PE PE2001000853A patent/PE20020393A1/en not_active Application Discontinuation
- 2001-08-24 UY UY26908A patent/UY26908A1/en not_active Application Discontinuation
- 2001-09-26 HN HN2001000216A patent/HN2001000216A/en unknown
-
2003
- 2003-02-12 ZA ZA200301182A patent/ZA200301182B/en unknown
- 2003-02-20 IS IS6724A patent/IS6724A/en unknown
- 2003-02-24 NO NO20030844A patent/NO20030844L/en not_active Application Discontinuation
- 2003-03-13 BG BG107635A patent/BG107635A/en unknown
- 2003-03-14 MA MA27069A patent/MA26949A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200301182B (en) | 2004-05-12 |
| PL360699A1 (en) | 2004-09-20 |
| GT200100174A (en) | 2002-07-18 |
| CN1458921A (en) | 2003-11-26 |
| IS6724A (en) | 2003-02-20 |
| HN2001000216A (en) | 2002-05-22 |
| PE20020393A1 (en) | 2002-05-09 |
| NO20030844D0 (en) | 2003-02-24 |
| EP1313694A1 (en) | 2003-05-28 |
| CA2420003A1 (en) | 2002-03-07 |
| PA8526501A1 (en) | 2002-07-30 |
| AU2001277044A1 (en) | 2002-03-13 |
| CZ2003477A3 (en) | 2003-10-15 |
| MA26949A1 (en) | 2004-12-20 |
| YU14303A (en) | 2006-08-17 |
| UY26908A1 (en) | 2001-11-30 |
| SK2072003A3 (en) | 2004-01-08 |
| EA200300187A1 (en) | 2003-08-28 |
| BG107635A (en) | 2004-09-30 |
| BR0113520A (en) | 2003-06-24 |
| SV2002000601A (en) | 2002-04-03 |
| DOP2001000238A (en) | 2003-01-31 |
| MXPA03001654A (en) | 2004-09-10 |
| TNSN01127A1 (en) | 2005-11-10 |
| KR20030059115A (en) | 2003-07-07 |
| WO2002018319A1 (en) | 2002-03-07 |
| JP2004507518A (en) | 2004-03-11 |
| IL154507A0 (en) | 2003-09-17 |
| NO20030844L (en) | 2003-02-25 |
| AR032175A1 (en) | 2003-10-29 |
| AP2001002249A0 (en) | 2001-09-30 |
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