CA2533433A1 - Novel n-substituted indolyl-3-glyoxylic acid amides, use thereof as a medicament, and method for the production thereof - Google Patents
Novel n-substituted indolyl-3-glyoxylic acid amides, use thereof as a medicament, and method for the production thereof Download PDFInfo
- Publication number
- CA2533433A1 CA2533433A1 CA002533433A CA2533433A CA2533433A1 CA 2533433 A1 CA2533433 A1 CA 2533433A1 CA 002533433 A CA002533433 A CA 002533433A CA 2533433 A CA2533433 A CA 2533433A CA 2533433 A1 CA2533433 A1 CA 2533433A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- general formula
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- -1 alkyl radical Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- KPFNPTVQXWKTOA-UHFFFAOYSA-N phenyl n-[2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxoacetyl]-n-quinolin-6-ylcarbamate Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)N(C(=O)OC=2C=CC=CC=2)C=2C=C3C=CC=NC3=CC=2)=C1 KPFNPTVQXWKTOA-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- GLCQUXKYTCTZJJ-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxo-n-(2-phenylacetyl)-n-quinolin-6-ylacetamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)N(C(=O)CC=2C=CC=CC=2)C=2C=C3C=CC=NC3=CC=2)=C1 GLCQUXKYTCTZJJ-UHFFFAOYSA-N 0.000 claims description 7
- BBPQAXFWNWTYBZ-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-n-(4-methylphenyl)sulfonyl-2-oxo-n-quinolin-6-ylacetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C=1C=C2C=CC=NC2=CC=1)C(=O)C(=O)C(C1=CC=CC=C11)=CN1CC1=CC=C(Cl)C=C1 BBPQAXFWNWTYBZ-UHFFFAOYSA-N 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- CQSKXMSYDKTHAQ-UHFFFAOYSA-N n-[2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxoacetyl]-n-quinolin-6-ylbenzamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)N(C(=O)C=2C=CC=CC=2)C=2C=C3C=CC=NC3=CC=2)=C1 CQSKXMSYDKTHAQ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 241000282412 Homo Species 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical group 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
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- KXAHCZGLIGKDEX-ACHDSSIZSA-N CC(C)[C@@H]1CC[C@@H](C)C[C@H]1C1=CC=C(C=C(C=C2)N(C(O)=O)C(=O)C(=O)C=3C4=CC=CC=C4N(CC=4C=CC(Cl)=CC=4)C=3)C2=N1 Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1C1=CC=C(C=C(C=C2)N(C(O)=O)C(=O)C(=O)C=3C4=CC=CC=C4N(CC=4C=CC(Cl)=CC=4)C=3)C2=N1 KXAHCZGLIGKDEX-ACHDSSIZSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000006386 neutralization reaction Methods 0.000 claims 2
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- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10334040A DE10334040A1 (de) | 2003-07-25 | 2003-07-25 | Neue N-substituierte Indolyl-3-glyoxylsäureamide, deren Verwendung als Arzneimittel und Verfahren zu deren Herstellung |
| DE10334040.8 | 2003-07-25 | ||
| PCT/EP2004/007573 WO2005014542A2 (de) | 2003-07-25 | 2004-07-09 | Neue n-substituierte indolyl-3-glyoxylsäureamide, deren verwendung als arzneimittel gegen krebs und verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2533433A1 true CA2533433A1 (en) | 2005-02-17 |
Family
ID=34129467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002533433A Abandoned CA2533433A1 (en) | 2003-07-25 | 2004-07-09 | Novel n-substituted indolyl-3-glyoxylic acid amides, use thereof as a medicament, and method for the production thereof |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1651600A2 (xx) |
| JP (1) | JP2007503376A (xx) |
| KR (1) | KR20060037398A (xx) |
| CN (1) | CN1839129A (xx) |
| AR (1) | AR045928A1 (xx) |
| AU (1) | AU2004263238A1 (xx) |
| BR (1) | BRPI0412898A (xx) |
| CA (1) | CA2533433A1 (xx) |
| DE (1) | DE10334040A1 (xx) |
| IL (1) | IL173335A0 (xx) |
| MX (1) | MXPA06000995A (xx) |
| NO (1) | NO20060697L (xx) |
| RS (1) | RS20060049A (xx) |
| RU (1) | RU2317293C9 (xx) |
| TW (1) | TW200524863A (xx) |
| UA (1) | UA83498C2 (xx) |
| WO (1) | WO2005014542A2 (xx) |
| ZA (1) | ZA200601300B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5406716B2 (ja) | 2006-08-07 | 2014-02-05 | アイアンウッド ファーマシューティカルズ インコーポレイテッド | インドール化合物 |
| AR084433A1 (es) | 2010-12-22 | 2013-05-15 | Ironwood Pharmaceuticals Inc | Inhibidores de la faah y composiciones farmaceuticas que los contienen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003022280A2 (en) * | 2001-09-13 | 2003-03-20 | Synta Pharmaceuticals Corp. | 3-glyoxlylamideindoles for treating cancer |
-
2003
- 2003-07-25 DE DE10334040A patent/DE10334040A1/de not_active Withdrawn
-
2004
- 2004-07-09 AU AU2004263238A patent/AU2004263238A1/en not_active Abandoned
- 2004-07-09 RU RU2006105708/04A patent/RU2317293C9/ru not_active IP Right Cessation
- 2004-07-09 MX MXPA06000995A patent/MXPA06000995A/es unknown
- 2004-07-09 EP EP04740854A patent/EP1651600A2/de not_active Withdrawn
- 2004-07-09 WO PCT/EP2004/007573 patent/WO2005014542A2/de active Application Filing
- 2004-07-09 BR BRPI0412898-2A patent/BRPI0412898A/pt not_active IP Right Cessation
- 2004-07-09 RS YUP-2006/0049A patent/RS20060049A/sr unknown
- 2004-07-09 JP JP2006521430A patent/JP2007503376A/ja not_active Withdrawn
- 2004-07-09 CN CNA2004800240832A patent/CN1839129A/zh active Pending
- 2004-07-09 KR KR1020067001636A patent/KR20060037398A/ko not_active Application Discontinuation
- 2004-07-09 CA CA002533433A patent/CA2533433A1/en not_active Abandoned
- 2004-07-19 TW TW093121509A patent/TW200524863A/zh unknown
- 2004-07-23 AR ARP040102632A patent/AR045928A1/es not_active Application Discontinuation
- 2004-09-07 UA UAA200601216A patent/UA83498C2/uk unknown
-
2006
- 2006-01-24 IL IL173335A patent/IL173335A0/en unknown
- 2006-02-13 ZA ZA200601300A patent/ZA200601300B/xx unknown
- 2006-02-14 NO NO20060697A patent/NO20060697L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL173335A0 (en) | 2006-06-11 |
| ZA200601300B (en) | 2007-03-28 |
| EP1651600A2 (de) | 2006-05-03 |
| RU2317293C2 (ru) | 2008-02-20 |
| DE10334040A1 (de) | 2005-03-10 |
| RU2006105708A (ru) | 2006-06-27 |
| JP2007503376A (ja) | 2007-02-22 |
| RU2317293C9 (ru) | 2008-05-10 |
| NO20060697L (no) | 2006-02-14 |
| RS20060049A (xx) | 2008-08-07 |
| TW200524863A (en) | 2005-08-01 |
| WO2005014542A3 (de) | 2006-10-19 |
| CN1839129A (zh) | 2006-09-27 |
| KR20060037398A (ko) | 2006-05-03 |
| AU2004263238A1 (en) | 2005-02-17 |
| BRPI0412898A (pt) | 2006-10-03 |
| MXPA06000995A (es) | 2006-04-11 |
| WO2005014542A2 (de) | 2005-02-17 |
| UA83498C2 (uk) | 2008-07-25 |
| AR045928A1 (es) | 2005-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |