RU2004126671A - Гетероарилсоединения, полезные в качестве ингибиторов gsk-3 - Google Patents
Гетероарилсоединения, полезные в качестве ингибиторов gsk-3Info
- Publication number
- RU2004126671A RU2004126671A RU2004126671/04A RU2004126671A RU2004126671A RU 2004126671 A RU2004126671 A RU 2004126671A RU 2004126671/04 A RU2004126671/04 A RU 2004126671/04A RU 2004126671 A RU2004126671 A RU 2004126671A RU 2004126671 A RU2004126671 A RU 2004126671A
- Authority
- RU
- Russia
- Prior art keywords
- benzoimidazol
- ring
- nitrogen
- optionally substituted
- furazan
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 15
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 title claims 2
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 title claims 2
- 239000003112 inhibitor Substances 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 34
- 229910052757 nitrogen Inorganic materials 0.000 claims 30
- 125000005842 heteroatom Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 18
- 239000001301 oxygen Substances 0.000 claims 18
- 125000004434 sulfur atom Chemical group 0.000 claims 18
- 238000000034 method Methods 0.000 claims 15
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- -1 4-aminofurazan-3-yl Chemical group 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 125000001118 alkylidene group Chemical group 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000001931 aliphatic group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- 206010020751 Hypersensitivity Diseases 0.000 claims 4
- 206010052779 Transplant rejections Diseases 0.000 claims 4
- 230000007815 allergy Effects 0.000 claims 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 201000006417 multiple sclerosis Diseases 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- AOYBLZGEIIBUTE-UHFFFAOYSA-N 1,2,5-oxadiazol-3-amine Chemical compound NC=1C=NON=1 AOYBLZGEIIBUTE-UHFFFAOYSA-N 0.000 claims 2
- GLQIZLCZHSQBLY-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1C1=NC2=CC=CC=C2N1 GLQIZLCZHSQBLY-UHFFFAOYSA-N 0.000 claims 2
- MWPXMWVHOXXWCY-UHFFFAOYSA-N 2-[2-(4-amino-1,2,5-oxadiazol-3-yl)benzimidazol-1-yl]-n-(2-phenylphenyl)acetamide Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC(=O)NC1=CC=CC=C1C1=CC=CC=C1 MWPXMWVHOXXWCY-UHFFFAOYSA-N 0.000 claims 2
- RKDKILJBYDCMPH-UHFFFAOYSA-N 2-[2-(4-amino-1,2,5-oxadiazol-3-yl)benzimidazol-1-yl]-n-(3,4-difluorophenyl)acetamide Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC(=O)NC1=CC=C(F)C(F)=C1 RKDKILJBYDCMPH-UHFFFAOYSA-N 0.000 claims 2
- IBQVTCXZQBZBDN-UHFFFAOYSA-N 2-[2-(4-amino-1,2,5-oxadiazol-3-yl)benzimidazol-1-yl]-n-(3-fluorophenyl)acetamide Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC(=O)NC1=CC=CC(F)=C1 IBQVTCXZQBZBDN-UHFFFAOYSA-N 0.000 claims 2
- DLHZNLYFGBAMAP-UHFFFAOYSA-N 2-[2-(4-amino-1,2,5-oxadiazol-3-yl)benzimidazol-1-yl]-n-tert-butylacetamide Chemical compound N=1C2=CC=CC=C2N(CC(=O)NC(C)(C)C)C=1C1=NON=C1N DLHZNLYFGBAMAP-UHFFFAOYSA-N 0.000 claims 2
- VFLJHDYRDURZEP-UHFFFAOYSA-N 2-[2-(4-amino-1,2,5-oxadiazol-3-yl)benzimidazol-1-yl]acetic acid Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC(O)=O VFLJHDYRDURZEP-UHFFFAOYSA-N 0.000 claims 2
- RSNMFVBZWSSWKA-UHFFFAOYSA-N 2-[2-(4-amino-1,2,5-oxadiazol-3-yl)benzimidazol-1-yl]acetonitrile Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC#N RSNMFVBZWSSWKA-UHFFFAOYSA-N 0.000 claims 2
- HCRQPXYLXXLKPT-UHFFFAOYSA-N 4-(1-ethylbenzimidazol-2-yl)-1,2,5-oxadiazol-3-amine Chemical compound N=1C2=CC=CC=C2N(CC)C=1C1=NON=C1N HCRQPXYLXXLKPT-UHFFFAOYSA-N 0.000 claims 2
- ZIHIDNWPEZFEMR-UHFFFAOYSA-N 4-(1-methylbenzimidazol-2-yl)-1,2,5-oxadiazol-3-amine Chemical compound N=1C2=CC=CC=C2N(C)C=1C1=NON=C1N ZIHIDNWPEZFEMR-UHFFFAOYSA-N 0.000 claims 2
- BKGOWPYQEFOGAO-UHFFFAOYSA-N 4-(1-prop-2-ynylbenzimidazol-2-yl)-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC#C BKGOWPYQEFOGAO-UHFFFAOYSA-N 0.000 claims 2
- OOQLAKYHQPZMKP-UHFFFAOYSA-N 4-(1-propan-2-ylbenzimidazol-2-yl)-1,2,5-oxadiazol-3-amine Chemical compound N=1C2=CC=CC=C2N(C(C)C)C=1C1=NON=C1N OOQLAKYHQPZMKP-UHFFFAOYSA-N 0.000 claims 2
- UZZWGLMVBYGQSK-UHFFFAOYSA-N 4-(1-propylbenzimidazol-2-yl)-1,2,5-oxadiazol-3-amine Chemical compound N=1C2=CC=CC=C2N(CCC)C=1C1=NON=C1N UZZWGLMVBYGQSK-UHFFFAOYSA-N 0.000 claims 2
- PAMMUBFLEAQXAD-UHFFFAOYSA-N 4-(6-methyl-1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-amine Chemical compound N=1C2=CC(C)=CC=C2NC=1C1=NON=C1N PAMMUBFLEAQXAD-UHFFFAOYSA-N 0.000 claims 2
- KNJOGMJHNSVZCC-UHFFFAOYSA-N 4-[1-(2h-tetrazol-5-ylmethyl)benzimidazol-2-yl]-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC1=NNN=N1 KNJOGMJHNSVZCC-UHFFFAOYSA-N 0.000 claims 2
- ROJIDUVOWRJHNV-UHFFFAOYSA-N 4-[1-[(2,4-dichlorophenyl)methyl]benzimidazol-2-yl]-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC1=CC=C(Cl)C=C1Cl ROJIDUVOWRJHNV-UHFFFAOYSA-N 0.000 claims 2
- GXKYZANVBKVGOS-UHFFFAOYSA-N 4-[1-[(2,6-dichlorophenyl)methyl]benzimidazol-2-yl]-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC1=C(Cl)C=CC=C1Cl GXKYZANVBKVGOS-UHFFFAOYSA-N 0.000 claims 2
- CPRADZBJYGDHHF-UHFFFAOYSA-N 4-[1-[(2-chloro-6-fluorophenyl)methyl]benzimidazol-2-yl]-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC1=C(F)C=CC=C1Cl CPRADZBJYGDHHF-UHFFFAOYSA-N 0.000 claims 2
- HIUITJWNRMJIBF-UHFFFAOYSA-N 4-[1-[(2-methylphenyl)methyl]benzimidazol-2-yl]-1,2,5-oxadiazol-3-amine Chemical compound CC1=CC=CC=C1CN1C2=CC=CC=C2N=C1C1=NON=C1N HIUITJWNRMJIBF-UHFFFAOYSA-N 0.000 claims 2
- VHBPIHGCMKHKLE-UHFFFAOYSA-N 4-[1-[(3,4-dichlorophenyl)methyl]benzimidazol-2-yl]-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 VHBPIHGCMKHKLE-UHFFFAOYSA-N 0.000 claims 2
- NSIJURZMDSCFBL-UHFFFAOYSA-N 4-[1-[(3-bromophenyl)methyl]benzimidazol-2-yl]-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC1=CC=CC(Br)=C1 NSIJURZMDSCFBL-UHFFFAOYSA-N 0.000 claims 2
- LAQLCMYZQGUKFA-UHFFFAOYSA-N 4-[1-[(4-chlorophenyl)methyl]benzimidazol-2-yl]-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CC1=CC=C(Cl)C=C1 LAQLCMYZQGUKFA-UHFFFAOYSA-N 0.000 claims 2
- ITWVPIOKFJWICI-UHFFFAOYSA-N 4-[1-[(4-methylphenyl)methyl]benzimidazol-2-yl]-1,2,5-oxadiazol-3-amine Chemical compound C1=CC(C)=CC=C1CN1C2=CC=CC=C2N=C1C1=NON=C1N ITWVPIOKFJWICI-UHFFFAOYSA-N 0.000 claims 2
- PQJCCZPMTJZYDF-UHFFFAOYSA-N 4-[2-(4-amino-1,2,5-oxadiazol-3-yl)benzimidazol-1-yl]butanenitrile Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1CCCC#N PQJCCZPMTJZYDF-UHFFFAOYSA-N 0.000 claims 2
- 206010065040 AIDS dementia complex Diseases 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010020880 Hypertrophy Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 238000007792 addition Methods 0.000 claims 2
- 231100000360 alopecia Toxicity 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 239000012472 biological sample Substances 0.000 claims 2
- QEPDSNAEMKSMGN-UHFFFAOYSA-N chembl1329127 Chemical compound NC1=NON=C1C1=NC2=CC=CC=C2N1 QEPDSNAEMKSMGN-UHFFFAOYSA-N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- OLGMRMJENRKJRP-UHFFFAOYSA-N n-[2-(1h-benzimidazol-2-yl)phenyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=CC=C1C1=NC2=CC=CC=C2N1 OLGMRMJENRKJRP-UHFFFAOYSA-N 0.000 claims 2
- IKUGCHSAVSKMEA-UHFFFAOYSA-N n-[2-(1h-benzimidazol-2-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C1=NC2=CC=CC=C2N1 IKUGCHSAVSKMEA-UHFFFAOYSA-N 0.000 claims 2
- VPCQBVROXHOCLQ-UHFFFAOYSA-N n-[2-(1h-benzimidazol-2-yl)phenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC=C1C1=NC2=CC=CC=C2N1 VPCQBVROXHOCLQ-UHFFFAOYSA-N 0.000 claims 2
- LGXJGCZIHDEMDL-UHFFFAOYSA-N n-[4-(1-ethylbenzimidazol-2-yl)-1,2,5-oxadiazol-3-yl]-2,2,2-trifluoroacetamide Chemical compound N=1C2=CC=CC=C2N(CC)C=1C1=NON=C1NC(=O)C(F)(F)F LGXJGCZIHDEMDL-UHFFFAOYSA-N 0.000 claims 2
- 230000010410 reperfusion Effects 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102000036243 Lymphocyte Specific Protein Tyrosine Kinase p56(lck) Human genes 0.000 claims 1
- 108010002481 Lymphocyte Specific Protein Tyrosine Kinase p56(lck) Proteins 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001555 benzenes Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- XUYDLORMICPNES-UHFFFAOYSA-N n-[4-[1-(cyanomethyl)benzimidazol-2-yl]-1,2,5-oxadiazol-3-yl]acetamide Chemical compound CC(=O)NC1=NON=C1C1=NC2=CC=CC=C2N1CC#N XUYDLORMICPNES-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Classifications
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
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| US35484302P | 2002-02-06 | 2002-02-06 | |
| US60/354,843 | 2002-02-06 |
Publications (1)
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| RU2004126671A true RU2004126671A (ru) | 2005-04-10 |
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| RU2004126671/04A RU2004126671A (ru) | 2002-02-06 | 2003-02-06 | Гетероарилсоединения, полезные в качестве ингибиторов gsk-3 |
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| US (2) | US20040034037A1 (https=) |
| EP (2) | EP2322521B1 (https=) |
| JP (2) | JP4656838B2 (https=) |
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| RU (1) | RU2004126671A (https=) |
| SG (1) | SG159380A1 (https=) |
| WO (1) | WO2003066629A2 (https=) |
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- 2003-02-06 US US10/360,535 patent/US20040034037A1/en not_active Abandoned
- 2003-02-06 ES ES10180554.7T patent/ES2437391T3/es not_active Expired - Lifetime
- 2003-02-06 RU RU2004126671/04A patent/RU2004126671A/ru not_active Application Discontinuation
- 2003-02-06 EP EP10180554.7A patent/EP2322521B1/en not_active Expired - Lifetime
- 2003-02-06 EP EP03710903A patent/EP1472245A2/en not_active Withdrawn
- 2003-02-06 CA CA2475633A patent/CA2475633C/en not_active Expired - Fee Related
- 2003-02-06 PL PL03372198A patent/PL372198A1/xx not_active Application Discontinuation
- 2003-02-06 MX MXPA04007697A patent/MXPA04007697A/es not_active Application Discontinuation
- 2003-02-06 KR KR10-2004-7012258A patent/KR20040084896A/ko not_active Withdrawn
- 2003-02-06 JP JP2003566002A patent/JP4656838B2/ja not_active Expired - Fee Related
- 2003-02-06 AU AU2003215087A patent/AU2003215087B2/en not_active Ceased
- 2003-02-06 SG SG200605228-6A patent/SG159380A1/en unknown
-
2004
- 2004-09-06 NO NO20043726A patent/NO20043726L/no unknown
-
2007
- 2007-07-12 US US11/776,756 patent/US20070270420A1/en not_active Abandoned
-
2010
- 2010-02-26 JP JP2010043557A patent/JP2010132697A/ja active Pending
Also Published As
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| PL372198A1 (en) | 2005-07-11 |
| MXPA04007697A (es) | 2004-11-10 |
| JP4656838B2 (ja) | 2011-03-23 |
| JP2005526028A (ja) | 2005-09-02 |
| AU2003215087A1 (en) | 2003-09-02 |
| US20040034037A1 (en) | 2004-02-19 |
| AU2003215087B2 (en) | 2009-07-16 |
| WO2003066629A3 (en) | 2003-10-30 |
| JP2010132697A (ja) | 2010-06-17 |
| EP2322521B1 (en) | 2013-09-04 |
| EP2322521A1 (en) | 2011-05-18 |
| CA2475633A1 (en) | 2003-08-14 |
| CA2475633C (en) | 2013-04-02 |
| WO2003066629A2 (en) | 2003-08-14 |
| US20070270420A1 (en) | 2007-11-22 |
| SG159380A1 (en) | 2010-03-30 |
| EP1472245A2 (en) | 2004-11-03 |
| KR20040084896A (ko) | 2004-10-06 |
| NO20043726L (no) | 2004-11-08 |
| ES2437391T3 (es) | 2014-01-10 |
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