SK1402001A3 - OXAZOLO, THIAZOLO AND SELENAZOLO [4,5-C]-QUINOLIN-4-AMINES ANDì (54) ANALOGS THEREOF - Google Patents

OXAZOLO, THIAZOLO AND SELENAZOLO [4,5-C]-QUINOLIN-4-AMINES ANDì (54) ANALOGS THEREOF Download PDF

Info

Publication number: SK1402001A3
Authority: SK; Slovakia
Prior art keywords: alkyl; quinolin; amine; quinoline; thiazolo
Prior art date: 1998-07-28

Application number

SK140-2001A

Other languages

English (en)

Slovak (sk)

Inventor

John F Gerster

Kyle J Lindstrom

Gregory J Marszalek

Bryon A Merrill

John W Mickelson

Michael J Rice

Original Assignee

3M Innovative Properties Co

Priority date (The priority date 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 date listed.)

1998-07-28

Filing date

1999-07-28

Publication date

2001-08-06

1999-07-28 Application filed by 3M Innovative Properties Co filed Critical 3M Innovative Properties Co

2001-08-06 Publication of SK1402001A3 publication Critical patent/SK1402001A3/sk

Links

150000001875 compounds Chemical class 0.000 claims abstract description 124
102000004127 Cytokines Human genes 0.000 claims abstract description 28
108090000695 Cytokines Proteins 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 25
230000015572 biosynthetic process Effects 0.000 claims abstract description 21
201000010099 disease Diseases 0.000 claims abstract description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
230000003612 virological effect Effects 0.000 claims abstract description 14
230000001613 neoplastic effect Effects 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 144
239000000203 mixture Substances 0.000 claims description 101
-1 2-methylthiazolo [4,5-c] quinolin-4-amine thiazolo [4,5-c] quinolin-4-amine 2-ethylthiazolo [4,5-c] quinolin-4-amine 2-propylthiazolo [4,5- c] quinolin-4-amine Chemical compound 0.000 claims description 48
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
239000011593 sulfur Substances 0.000 claims description 19
241001465754 Metazoa Species 0.000 claims description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 14
108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 13
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
NFYMGJSUKCDVJR-UHFFFAOYSA-N 2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 NFYMGJSUKCDVJR-UHFFFAOYSA-N 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
125000001072 heteroaryl group Chemical group 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
102000006992 Interferon-alpha Human genes 0.000 claims description 10
108010047761 Interferon-alpha Proteins 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 6
229910052711 selenium Inorganic materials 0.000 claims description 6
239000011669 selenium Substances 0.000 claims description 6
MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 claims description 5
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
230000001939 inductive effect Effects 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
150000001555 benzenes Chemical group 0.000 claims 3
229910052684 Cerium Inorganic materials 0.000 claims 1
102000014150 Interferons Human genes 0.000 abstract description 23
108010050904 Interferons Proteins 0.000 abstract description 23
229940079322 interferon Drugs 0.000 abstract description 20
238000004519 manufacturing process Methods 0.000 abstract description 7
206010028980 Neoplasm Diseases 0.000 abstract description 6
230000028993 immune response Effects 0.000 abstract description 6
239000000543 intermediate Substances 0.000 abstract description 5
239000002955 immunomodulating agent Substances 0.000 abstract description 3
229940121354 immunomodulator Drugs 0.000 abstract description 3
HLVNSLBJOPUZKV-UHFFFAOYSA-N [1,3]selenazolo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=C[se]2 HLVNSLBJOPUZKV-UHFFFAOYSA-N 0.000 abstract 1
230000017074 necrotic cell death Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 384
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 249
239000011541 reaction mixture Substances 0.000 description 170
239000007787 solid Substances 0.000 description 166
229910052757 nitrogen Inorganic materials 0.000 description 125
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 122
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
229910052799 carbon Inorganic materials 0.000 description 105
239000000243 solution Substances 0.000 description 99
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 96
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
238000004458 analytical method Methods 0.000 description 84
239000002244 precipitate Substances 0.000 description 67
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
238000001914 filtration Methods 0.000 description 59
238000006243 chemical reaction Methods 0.000 description 58
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 50
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 49
229910052943 magnesium sulfate Inorganic materials 0.000 description 48
235000019341 magnesium sulphate Nutrition 0.000 description 48
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
238000010992 reflux Methods 0.000 description 41
239000000725 suspension Substances 0.000 description 41
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 40
239000000463 material Substances 0.000 description 39
239000000706 filtrate Substances 0.000 description 34
238000007429 general method Methods 0.000 description 31
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 29
239000003921 oil Substances 0.000 description 27
235000019198 oils Nutrition 0.000 description 27
GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
239000000047 product Substances 0.000 description 23
229910000030 sodium bicarbonate Inorganic materials 0.000 description 23
235000017557 sodium bicarbonate Nutrition 0.000 description 23
150000001204 N-oxides Chemical class 0.000 description 20
FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 19
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 19
235000011114 ammonium hydroxide Nutrition 0.000 description 19
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 18
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000000908 ammonium hydroxide Substances 0.000 description 18
239000012299 nitrogen atmosphere Substances 0.000 description 18
239000012043 crude product Substances 0.000 description 17
239000000284 extract Substances 0.000 description 17
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
239000000843 powder Substances 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
210000004027 cell Anatomy 0.000 description 15
239000003795 chemical substances by application Substances 0.000 description 15
239000012044 organic layer Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
229910021529 ammonia Inorganic materials 0.000 description 14
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 14
239000010410 layer Substances 0.000 description 13
238000004809 thin layer chromatography Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000001408 amides Chemical class 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
230000006698 induction Effects 0.000 description 12
239000012948 isocyanate Substances 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
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ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
238000003756 stirring Methods 0.000 description 11
239000006188 syrup Substances 0.000 description 11
235000020357 syrup Nutrition 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 10
239000012267 brine Substances 0.000 description 10
150000002513 isocyanates Chemical class 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
229940086542 triethylamine Drugs 0.000 description 10
239000002253 acid Substances 0.000 description 9
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
YJBLTYRYUXKJLE-UHFFFAOYSA-N 3-amino-1h-quinoline-4-thione Chemical compound C1=CC=C2C(=S)C(N)=CNC2=C1 YJBLTYRYUXKJLE-UHFFFAOYSA-N 0.000 description 8
OWHMGQJEHHCWCJ-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(SC=N3)C3=CN=C21 OWHMGQJEHHCWCJ-UHFFFAOYSA-N 0.000 description 8
239000012298 atmosphere Substances 0.000 description 8
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
NIQNIQVCPKCNQS-UHFFFAOYSA-N 3-amino-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)C(N)=CNC2=C1 NIQNIQVCPKCNQS-UHFFFAOYSA-N 0.000 description 7
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
239000008280 blood Substances 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
210000005260 human cell Anatomy 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
229910017604 nitric acid Inorganic materials 0.000 description 7
238000012360 testing method Methods 0.000 description 7
ZDENTSZZTCBRAM-UHFFFAOYSA-N 2-ethyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(CC)=N3)C3=C(N)N=C21 ZDENTSZZTCBRAM-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
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238000004587 chromatography analysis Methods 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
238000004896 high resolution mass spectrometry Methods 0.000 description 6
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238000002360 preparation method Methods 0.000 description 6
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238000003786 synthesis reaction Methods 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 5
LYXUZFHABUMMBT-UHFFFAOYSA-N 2-methyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(C)=N3)C3=C(N)N=C21 LYXUZFHABUMMBT-UHFFFAOYSA-N 0.000 description 5
238000002965 ELISA Methods 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
239000001569 carbon dioxide Substances 0.000 description 5
229910002092 carbon dioxide Inorganic materials 0.000 description 5
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238000005576 amination reaction Methods 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
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HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
238000011953 bioanalysis Methods 0.000 description 4
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 4
230000000120 cytopathologic effect Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002367 halogens Chemical group 0.000 description 4
230000003301 hydrolyzing effect Effects 0.000 description 4
125000004356 hydroxy functional group Chemical group O* 0.000 description 4
238000011534 incubation Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
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BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
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230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 4
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150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
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239000003279 phenylacetic acid Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
201000000317 pneumocystosis Diseases 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
230000008569 process Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
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239000000523 sample Substances 0.000 description 1
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229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
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150000003431 steroids Chemical class 0.000 description 1
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TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
230000004565 tumor cell growth Effects 0.000 description 1
230000029069 type 2 immune response Effects 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A61P31/04—Antibacterial agents
- 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
- A61P31/10—Antimycotics
- 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
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
- C07D517/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Immunology (AREA)
Neurology (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Virology (AREA)
Psychiatry (AREA)
Orthopedic Medicine & Surgery (AREA)
Tropical Medicine & Parasitology (AREA)
Dermatology (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Photoreceptors In Electrophotography (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

SK140-2001A 1998-07-28 1999-07-28 OXAZOLO, THIAZOLO AND SELENAZOLO [4,5-C]-QUINOLIN-4-AMINES ANDì (54) ANALOGS THEREOF SK1402001A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US9434698P	1998-07-28	1998-07-28
US09/361,544 US6110929A (en)	1998-07-28	1999-07-27	Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof
PCT/US1999/017027 WO2000006577A1 (fr)	1998-07-28	1999-07-28	OXAZOLO, THIAZOLO ET SELENAZOLO [4,5-c]-QUINOLINE-4-AMINES ET LEURS ANALOGUES

Publications (1)

Publication Number	Publication Date
SK1402001A3 true SK1402001A3 (en)	2001-08-06

Family

ID=26788753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK140-2001A SK1402001A3 (en)	1998-07-28	1999-07-28	OXAZOLO, THIAZOLO AND SELENAZOLO [4,5-C]-QUINOLIN-4-AMINES ANDì (54) ANALOGS THEREOF

Country Status (24)

Country	Link
US (9)	US6110929A (fr)
EP (1)	EP1100802B1 (fr)
JP (1)	JP4662630B2 (fr)
KR (1)	KR100696349B1 (fr)
CN (1)	CN1147493C (fr)
AT (2)	ATE320435T1 (fr)
AU (1)	AU748050B2 (fr)
BR (1)	BR9912448A (fr)
CA (1)	CA2338504C (fr)
CZ (1)	CZ291753B6 (fr)
DE (2)	DE69930327T2 (fr)
DK (1)	DK1100802T3 (fr)
ES (2)	ES2203160T3 (fr)
HU (1)	HUP0103137A3 (fr)
IL (1)	IL140822A0 (fr)
MX (1)	MXPA01000757A (fr)
NO (1)	NO20010497L (fr)
NZ (1)	NZ509420A (fr)
PL (1)	PL347590A1 (fr)
PT (2)	PT1380587E (fr)
RU (1)	RU2244717C2 (fr)
SK (1)	SK1402001A3 (fr)
TR (1)	TR200100278T2 (fr)
WO (1)	WO2000006577A1 (fr)

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US6110929A (en) *	1998-07-28	2000-08-29	3M Innovative Properties Company	Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof
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US20020058674A1 (en)	1999-01-08	2002-05-16	Hedenstrom John C.	Systems and methods for treating a mucosal surface
EP1140091B1 (fr)	1999-01-08	2005-09-21	3M Innovative Properties Company	Formulations pour le traitement de la dysplasie cervicale au moyen d'un modificateur de la reponse immunitaire
US6486168B1 (en)	1999-01-08	2002-11-26	3M Innovative Properties Company	Formulations and methods for treatment of mucosal associated conditions with an immune response modifier
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US6525064B1 (en)	2000-12-08	2003-02-25	3M Innovative Properties Company	Sulfonamido substituted imidazopyridines
US6677348B2 (en)	2000-12-08	2004-01-13	3M Innovative Properties Company	Aryl ether substituted imidazoquinolines
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AU2002232498B2 (en) *	2000-12-08	2006-05-04	3M Innovative Properties Company	Screening method for identifying compounds that selectively induce interferon alpha
US6667312B2 (en) *	2000-12-08	2003-12-23	3M Innovative Properties Company	Thioether substituted imidazoquinolines
US6545017B1 (en)	2000-12-08	2003-04-08	3M Innovative Properties Company	Urea substituted imidazopyridines
UA74852C2 (en)	2000-12-08	2006-02-15	3M Innovative Properties Co	Urea-substituted imidazoquinoline ethers
US6545016B1 (en)	2000-12-08	2003-04-08	3M Innovative Properties Company	Amide substituted imidazopyridines
US6664265B2 (en)	2000-12-08	2003-12-16	3M Innovative Properties Company	Amido ether substituted imidazoquinolines
US6677347B2 (en) *	2000-12-08	2004-01-13	3M Innovative Properties Company	Sulfonamido ether substituted imidazoquinolines
US7226928B2 (en) *	2001-06-15	2007-06-05	3M Innovative Properties Company	Methods for the treatment of periodontal disease
JP2005501550A (ja) *	2001-08-30	2005-01-20	スリーエムイノベイティブプロパティズカンパニー	免疫反応調整剤分子を用いた形質細胞様樹状細胞を成熟させる方法
CA2462203A1 (fr) *	2001-10-12	2003-11-20	University Of Iowa Research Foundation	Methodes et produits permettant d'ameliorer des reponses immunitaires a l'aide de compose d'imidazoquinoline
AU2002343728A1 (en) *	2001-11-16	2003-06-10	3M Innovative Properties Company	Methods and compositions related to irm compounds and toll-like receptor pathways
CA2467828C (fr) *	2001-11-29	2011-10-04	3M Innovative Properties Company	Formulations pharmaceutiques comprenant un modificateur de reponse immunitaire
CA2365732A1 (fr) *	2001-12-20	2003-06-20	Ibm Canada Limited-Ibm Canada Limitee	Etalonnages
US6677349B1 (en) *	2001-12-21	2004-01-13	3M Innovative Properties Company	Sulfonamide and sulfamide substituted imidazoquinolines
DK1471974T3 (da) *	2002-02-06	2007-12-03	Ares Trading Sa	Tumornekrose-faktor kombineret med interferon ved demyeliniserende sygdomme
US7030129B2 (en) *	2002-02-22	2006-04-18	3M Innovative Properties Company	Method of reducing and treating UVB-induced immunosuppression
DE60325838D1 (de) *	2002-03-19	2009-03-05	Glaxo Group Ltd	Imidazoquinolinamine als adjuvantien für hiv dna vakzine
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- 1999-07-28 RU RU2001102777/04A patent/RU2244717C2/ru not_active IP Right Cessation
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Publication number	Publication date
ATE250612T1 (de)	2003-10-15
DE69911622D1 (de)	2003-10-30
CN1320126A (zh)	2001-10-31
PT1380587E (pt)	2006-08-31
US6809203B2 (en)	2004-10-26
PL347590A1 (en)	2002-04-08
CZ2001327A3 (cs)	2001-08-15
US6677334B2 (en)	2004-01-13
CZ291753B6 (cs)	2003-05-14
HUP0103137A3 (en)	2002-06-28
DK1100802T3 (da)	2004-02-09
CA2338504C (fr)	2011-03-08
KR20010085309A (ko)	2001-09-07
DE69911622T2 (de)	2004-06-17
US20020072528A1 (en)	2002-06-13
CN1147493C (zh)	2004-04-28
US20030045545A1 (en)	2003-03-06
IL140822A0 (en)	2002-02-10
JP2002524392A (ja)	2002-08-06
DE69930327T2 (de)	2006-12-07
MXPA01000757A (es)	2002-04-08
EP1100802B1 (fr)	2003-09-24
RU2244717C2 (ru)	2005-01-20
US6440992B1 (en)	2002-08-27
JP4662630B2 (ja)	2011-03-30
NO20010497L (no)	2001-03-27
KR100696349B1 (ko)	2007-03-20
HUP0103137A2 (hu)	2002-01-28
TR200100278T2 (tr)	2001-08-21
ES2203160T3 (es)	2004-04-01
US20040122041A1 (en)	2004-06-24
US6703402B2 (en)	2004-03-09
US20030195224A1 (en)	2003-10-16
EP1100802A1 (fr)	2001-05-23
US6627638B2 (en)	2003-09-30
US20030064968A1 (en)	2003-04-03
US6323200B1 (en)	2001-11-27
CA2338504A1 (fr)	2000-02-10
US7148232B2 (en)	2006-12-12
AU5133199A (en)	2000-02-21
BR9912448A (pt)	2001-10-09
WO2000006577A1 (fr)	2000-02-10
AU748050B2 (en)	2002-05-30
PT1100802E (pt)	2004-02-27
US20050026943A1 (en)	2005-02-03
NO20010497D0 (no)	2001-01-29
US6627640B2 (en)	2003-09-30
US20030065006A1 (en)	2003-04-03
NZ509420A (en)	2003-08-29
ES2260554T3 (es)	2006-11-01
US6110929A (en)	2000-08-29
HK1038228A1 (en)	2002-03-08
DE69930327D1 (de)	2006-05-11
ATE320435T1 (de)	2006-04-15

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