HUP0203405A2 - A substituted phenylenediamine group and heterocyclic carboxamide group containing thiourea derivatives inhibitors of herpes viruses, pharmaceutical compositions containing them and their use - Google Patents
A substituted phenylenediamine group and heterocyclic carboxamide group containing thiourea derivatives inhibitors of herpes viruses, pharmaceutical compositions containing them and their useInfo
- Publication number
- HUP0203405A2 HUP0203405A2 HU0203405A HUP0203405A HUP0203405A2 HU P0203405 A2 HUP0203405 A2 HU P0203405A2 HU 0203405 A HU0203405 A HU 0203405A HU P0203405 A HUP0203405 A HU P0203405A HU P0203405 A2 HUP0203405 A2 HU P0203405A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- alkyl
- hydrogen atom
- perhaloalkyl
- heterocycloalkyl
- Prior art date
Links
- 241001529453 unidentified herpesvirus Species 0.000 title abstract 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical group NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003585 thioureas Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 3
- -1 cyano- Chemical class 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 241000701085 Human alphaherpesvirus 3 Species 0.000 abstract 1
- 241000701024 Human betaherpesvirus 5 Species 0.000 abstract 1
- 241000701041 Human betaherpesvirus 7 Species 0.000 abstract 1
- 241000701044 Human gammaherpesvirus 4 Species 0.000 abstract 1
- 241000701027 Human herpesvirus 6 Species 0.000 abstract 1
- 241000700584 Simplexvirus Species 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000304 alkynyl 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
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
A találmány (I) általános képletű vegyületekre és gyógyászatilagelfogadható sóikra vonatkozik, ahol R1R5 jelentése hidrogénatom,alkil-, alkenil-, alkinil-, perhalogénalkil-, cikloalkil-,heterocikloalkil-, aril-, heteroarilcsoport, halogénatom, ciano-,nitrocsoport, -CO2R6, -COR6, -OR6, -SR6, -SOR6, -SO2R6, -CONR7R8, -NR6N(R7R8), -N(R7R8) vagy W-Y-(CH2)n-Z csoport, azzal a megkötéssel,hogy az R1-R5 csoportok közül legalább egy nem hidrogénatom; vagy R2és R3 vagy R3 és R4 együtt heterocikloalkilcsoportot vagyheteroarilcsoportot alkot; R6 és R7 jelentése hidrogénatom, alkil-,perhalogénalkil-, vagy arilcsoport; R8 jelentése hidrogénatom, alkil-,perhalogénalkil-, cikloalkil-, heterocikloalkil-, aril-,heteroarilcsoport, vagy R7 és R8 együtt heterocikloalkilcsoportotalkothat; R9 - R12 jelentése hidrogénatom, alkil-, perhalogénalkil-,halogénatom, alkoxi-, cianocsoport vagy R9 és R10 vagy R11 es R12arilcsoportot alkothat, azzal a megkötéssel, hogy az R9 - R12csoportok közül legalább egynek a jelentése nem hidrogénatom; Wjelentése oxigénatom, -NR6 általános képletű csoport, vagy hiányzik; Yjelentése -(CO)- vagy -(CO2)-, vagy hiányzik; Z jelentése alkil-,cianocsoport, -CO2R6, -COR6, -CONR7R8, -OCOR6, -NR6COR7, -OCONR6, -OR6, -SR6, -SOR6, -SO2R6, SR6N(R7R8), -N(R7R8) vagy fenilcsoport; Gjelentése monociklusos heteroarilcsoport; X jelentése vegyértékkötés,-NH-, alkil-, alkenil-, alkoxi-, alkil-tio-, alkil-amino-csoport vagy(CH)J csoport; J jelentése alkil-, cikloalkil-, fenil- vagybenzilcsoport; és n értéke 1-6. A vegyületek gátolják és/vagygyógyítják a herpeszvírusok, például a humán citomegalovírusok,herpesz szimplex vírusok, Epstein-Barr vírus, varicella-zoster vírus,humán herpeszvírus-6 és -7 és a Kaposi herpeszvírus által okozottbetegségeket. A találmány a vegyületeket tartalmazógyógyszerkészítményekre és a vegyületek alkalmazására is vonatkozik. ÓThe invention relates to compounds of general formula (I) and their pharmaceutically acceptable salts, where R1R5 is a hydrogen atom, alkyl-, alkenyl-, alkynyl-, perhaloalkyl-, cycloalkyl-, heterocycloalkyl-, aryl-, heteroaryl group, halogen atom, cyano-, nitro group, -CO2R6 . at least one non-hydrogen atom; or R 2 and R 3 or R 3 and R 4 together form a heterocycloalkyl group or a heteroaryl group; R 6 and R 7 are hydrogen, alkyl, perhaloalkyl or aryl; R8 represents a hydrogen atom, an alkyl, perhaloalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl group, or R7 and R8 can together form a heterocycloalkyl group; R9 - R12 is a hydrogen atom, alkyl, perhaloalkyl, halogen atom, alkoxy, cyano group or R9 and R10 or R11 can form an R12aryl group, with the stipulation that at least one of the R9 - R12 groups is not a hydrogen atom; W is an oxygen atom, a group of formula -NR6, or is absent; Y means -(CO)- or -(CO2)-, or absent; Z is alkyl, cyano, -CO2R6, -COR6, -CONR7R8, -OCOR6, -NR6COR7, -OCONR6, -OR6, -SR6, -SOR6, -SO2R6, SR6N(R7R8), -N(R7R8) or phenyl; G represents a monocyclic heteroaryl group; X is a valence bond, -NH-, alkyl-, alkenyl-, alkoxy-, alkylthio-, alkylamino group or (CH)J group; J is alkyl, cycloalkyl, phenyl or benzyl; and n is 1-6. The compounds inhibit and/or cure diseases caused by herpes viruses, such as human cytomegalovirus, herpes simplex virus, Epstein-Barr virus, varicella-zoster virus, human herpesvirus-6 and -7, and Kaposi's herpesvirus. The invention also relates to pharmaceutical preparations containing the compounds and to the use of the compounds. HE
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20816498A | 1998-12-09 | 1998-12-09 | |
| PCT/US1999/028916 WO2000034261A2 (en) | 1998-12-09 | 1999-12-06 | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0203405A2 true HUP0203405A2 (en) | 2003-02-28 |
Family
ID=22773466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0203405A HUP0203405A2 (en) | 1998-12-09 | 1999-12-06 | A substituted phenylenediamine group and heterocyclic carboxamide group containing thiourea derivatives inhibitors of herpes viruses, pharmaceutical compositions containing them and their use |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1144399A3 (en) |
| JP (1) | JP2002533301A (en) |
| KR (1) | KR20010086091A (en) |
| CN (1) | CN1367785A (en) |
| AU (1) | AU2353900A (en) |
| BR (1) | BR9916043A (en) |
| CA (1) | CA2351690A1 (en) |
| CZ (1) | CZ20012063A3 (en) |
| EA (1) | EA200100639A1 (en) |
| HU (1) | HUP0203405A2 (en) |
| IL (1) | IL143263A0 (en) |
| NO (1) | NO20012835L (en) |
| WO (1) | WO2000034261A2 (en) |
| ZA (1) | ZA200104322B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6844367B1 (en) | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
| WO2001064642A2 (en) | 2000-02-29 | 2001-09-07 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| EA010017B1 (en) * | 2003-07-10 | 2008-06-30 | Ачиллион Фармасьютикалз, Инк. | Substituted arylthiourea derivatives useful as inhibitors of viral replication |
| DE102004015007A1 (en) * | 2004-03-26 | 2005-10-13 | Bayer Healthcare Ag | Substituted imidazoles |
| TW200600492A (en) | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
| DE102005008183A1 (en) | 2005-02-23 | 2006-08-31 | Bayer Healthcare Ag | New heterocyclylamide-substituted imidazole compounds useful to treat or prevent viral infections |
| PT2077995E (en) | 2006-11-02 | 2012-05-10 | Millennium Pharm Inc | Methods of synthesizing pharmaceutical salts of a factor xa inhibitor |
| US9334249B2 (en) | 2012-11-03 | 2016-05-10 | Boehringer Ingelheim International Gmbh | Inhibitors of cytomegalovirus |
| JP6482466B2 (en) * | 2012-11-03 | 2019-03-13 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Cytomegalovirus inhibitors |
| CN112807294B (en) * | 2019-11-18 | 2023-09-05 | 武汉大学 | Application of acyl thiourea compound in preparation of medicines for treating or preventing herpes simplex virus type I infection |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69830751T2 (en) * | 1997-04-10 | 2006-05-18 | Pharmacia & Upjohn Co. Llc, Kalamazoo | Polyaromatic compounds for the treatment of herpes infections |
-
1999
- 1999-12-06 CZ CZ20012063A patent/CZ20012063A3/en unknown
- 1999-12-06 EP EP99967213A patent/EP1144399A3/en not_active Withdrawn
- 1999-12-06 BR BR9916043-9A patent/BR9916043A/en not_active Application Discontinuation
- 1999-12-06 CA CA002351690A patent/CA2351690A1/en not_active Abandoned
- 1999-12-06 JP JP2000586708A patent/JP2002533301A/en active Pending
- 1999-12-06 IL IL14326399A patent/IL143263A0/en unknown
- 1999-12-06 AU AU23539/00A patent/AU2353900A/en not_active Abandoned
- 1999-12-06 KR KR1020017007117A patent/KR20010086091A/en not_active Application Discontinuation
- 1999-12-06 HU HU0203405A patent/HUP0203405A2/en unknown
- 1999-12-06 EA EA200100639A patent/EA200100639A1/en unknown
- 1999-12-06 WO PCT/US1999/028916 patent/WO2000034261A2/en not_active Application Discontinuation
- 1999-12-06 CN CN99815998A patent/CN1367785A/en active Pending
-
2001
- 2001-05-25 ZA ZA200104322A patent/ZA200104322B/en unknown
- 2001-06-08 NO NO20012835A patent/NO20012835L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CZ20012063A3 (en) | 2001-10-17 |
| NO20012835D0 (en) | 2001-06-08 |
| EP1144399A3 (en) | 2002-09-11 |
| IL143263A0 (en) | 2002-04-21 |
| EP1144399A2 (en) | 2001-10-17 |
| EA200100639A1 (en) | 2002-06-27 |
| AU2353900A (en) | 2000-06-26 |
| JP2002533301A (en) | 2002-10-08 |
| NO20012835L (en) | 2001-07-19 |
| BR9916043A (en) | 2001-12-04 |
| WO2000034261A2 (en) | 2000-06-15 |
| CA2351690A1 (en) | 2000-06-15 |
| WO2000034261A3 (en) | 2002-01-31 |
| ZA200104322B (en) | 2002-10-25 |
| CN1367785A (en) | 2002-09-04 |
| KR20010086091A (en) | 2001-09-07 |
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