DE19935219A1 - Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung - Google Patents
Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und HerstellungInfo
- Publication number
- DE19935219A1 DE19935219A1 DE19935219A DE19935219A DE19935219A1 DE 19935219 A1 DE19935219 A1 DE 19935219A1 DE 19935219 A DE19935219 A DE 19935219A DE 19935219 A DE19935219 A DE 19935219A DE 19935219 A1 DE19935219 A1 DE 19935219A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- alkyl
- phenyl
- trans
- carboxy
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 title claims abstract description 8
- 150000003857 carboxamides Chemical class 0.000 title claims description 17
- 229940079593 drug Drugs 0.000 title claims description 4
- 108010017842 Telomerase Proteins 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 13
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 4
- -1 monosubstituted phenyl Chemical group 0.000 claims description 108
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 103
- 239000000460 chlorine Substances 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 64
- 125000003545 alkoxy group Chemical group 0.000 claims description 59
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 54
- 229910052801 chlorine Inorganic materials 0.000 claims description 50
- 229910052731 fluorine Inorganic materials 0.000 claims description 50
- 150000001408 amides Chemical class 0.000 claims description 47
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 46
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 46
- 239000011737 fluorine Substances 0.000 claims description 46
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 39
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
- 125000001624 naphthyl group Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 22
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 22
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000004434 sulfur atom Chemical group 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 238000001727 in vivo Methods 0.000 claims description 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 10
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000005277 alkyl imino group Chemical group 0.000 claims description 9
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 8
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical group C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 6
- 238000005917 acylation reaction Methods 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 230000001681 protective effect Effects 0.000 claims description 6
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 230000004962 physiological condition Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 230000006103 sulfonylation Effects 0.000 claims description 4
- 238000005694 sulfonylation reaction Methods 0.000 claims description 4
- 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 3
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 2
- DMSHWWDRAYHEBS-UHFFFAOYSA-N dihydrocoumarin Natural products C1CC(=O)OC2=C1C=C(OC)C(OC)=C2 DMSHWWDRAYHEBS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 571
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 483
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 299
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 222
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 166
- 239000000741 silica gel Substances 0.000 description 166
- 229910002027 silica gel Inorganic materials 0.000 description 166
- 238000001819 mass spectrum Methods 0.000 description 154
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 144
- 239000000243 solution Substances 0.000 description 116
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 112
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 56
- 229940086542 triethylamine Drugs 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000011734 sodium Substances 0.000 description 34
- FPQMGQZTBWIHDN-UHFFFAOYSA-N 5-fluoroanthranilic acid Chemical compound NC1=CC=C(F)C=C1C(O)=O FPQMGQZTBWIHDN-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000003208 petroleum Substances 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 10
- 206010028980 Neoplasm Diseases 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
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- 108020004414 DNA Proteins 0.000 description 9
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- 239000000284 extract Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
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- 235000019359 magnesium stearate Nutrition 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 229920002261 Corn starch Polymers 0.000 description 7
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
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- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 6
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
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- 238000005119 centrifugation Methods 0.000 description 4
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- 238000012546 transfer Methods 0.000 description 4
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by 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
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Engineering & Computer Science (AREA)
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- Immunology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19935219A DE19935219A1 (de) | 1999-07-27 | 1999-07-27 | Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
| US09/618,702 US6362210B1 (en) | 1999-07-27 | 2000-07-18 | Carboxylic acid amides, pharmaceutical compositions containing these compounds and their use |
| SK296-2002A SK2962002A3 (en) | 1999-07-27 | 2000-07-22 | Carboxylic acid amides, medicaments containing these compounds and the use and production thereof |
| AU64368/00A AU6436800A (en) | 1999-07-27 | 2000-07-22 | Carboxylic acid amides, medicaments containing these compounds and the use and production thereof |
| CN00812829A CN1414849A (zh) | 1999-07-27 | 2000-07-22 | 羧酸酰胺,包含该化合物的药物组合物,其用途及制备 |
| MXPA02000822A MXPA02000822A (es) | 1999-07-27 | 2000-07-22 | Amidas de acidos carboxilicos, medicamentos que contienen estos compuestos, su utilizacion y su preparacion. |
| YU5502A YU5502A (sh) | 1999-07-27 | 2000-07-22 | Amidi karbonskih kiselina, lekovi koji sadrže ova jedinjenja, njihova upotreba i proizvodnja |
| EP00951431A EP1261321A2 (de) | 1999-07-27 | 2000-07-22 | Carbonsäureamide, diese verbindungen enthaltende arzneimittel, deren verwendung und herstellung |
| CZ2002313A CZ2002313A3 (cs) | 1999-07-27 | 2000-07-22 | Amidy karboxylových kyselin |
| EEP200200041A EE200200041A (et) | 1999-07-27 | 2000-07-22 | Karboksüülhappeamiidid, neid ühendeid sisaldavad ravimid, nende kasutamine ja valmistamine |
| HU0204373A HUP0204373A3 (en) | 1999-07-27 | 2000-07-22 | Carboxylic acid amides, pharmaceutical compositions containing these compounds and the use and production thereof |
| EA200200114A EA200200114A1 (ru) | 1999-07-27 | 2000-07-22 | Амиды карбоновой кислоты, содержащие эти соединения лекарственные средства, их применение и получение |
| TR2002/00226T TR200200226T2 (tr) | 1999-07-27 | 2000-07-22 | Karbonasitamidler, bu bileşikleri ihtiva eden ilaç, kullanımı ve üretimi. |
| KR1020027001103A KR20020032537A (ko) | 1999-07-27 | 2000-07-22 | 카복실산 아미드, 이를 함유하는 약제, 이의 용도 및 이의제조방법 |
| BR0013184-9A BR0013184A (pt) | 1999-07-27 | 2000-07-22 | Amidas de ácido carboxìlico, composições farmacêuticas contendo estes compostos, uso e preparação destes |
| PL36133500A PL361335A1 (en) | 1999-07-27 | 2000-07-22 | Carboxylic acid amides, medicaments containing these compounds and the use and production thereof |
| PCT/EP2000/007057 WO2001007020A2 (de) | 1999-07-27 | 2000-07-22 | Carbonsäureamide, diese verbindungen enthaltende arzneimittel, deren verwendung und herstellung |
| JP2001511906A JP5010788B2 (ja) | 1999-07-27 | 2000-07-22 | カルボン酸アミド、その化合物を含有する医薬組成物、その使用及び調製 |
| HR20020072A HRP20020072A2 (en) | 1999-07-27 | 2000-07-22 | Carboxylic acid amides, medicaments containing these compounds and the use and production thereof |
| CA002378382A CA2378382C (en) | 1999-07-27 | 2000-07-22 | Carboxylic acid amides, pharmaceutical compositions containing these compounds, the use and preparation thereof |
| IL14770700A IL147707A0 (en) | 1999-07-27 | 2000-07-22 | Carboxylic acid amides, medicaments containing these compounds and the use and production thereof |
| UY26256A UY26256A1 (es) | 1999-07-27 | 2000-07-25 | Amidas de ácidos carboxílicos, medicamentos que contienen estos compuestos, su utilización y su preparación |
| ARP000103858A AR024944A1 (es) | 1999-07-27 | 2000-07-26 | Amidas de acidos carboxilicos, medicamentos que contienen estos compuestos, su utilizacion y su preparacion |
| CO00056547A CO5180639A1 (es) | 1999-07-27 | 2000-07-27 | Amidas de acidos carboxilicos medicamentos que contienen estos compuestos su utilizacion y su prepracion |
| US10/037,555 US6727250B2 (en) | 1999-07-27 | 2002-01-03 | Carboxylic acid amides, pharmaceutical compositions containing these compounds, their use and preparation |
| BG106343A BG106343A (bg) | 1999-07-27 | 2002-01-23 | Амиди на карбоксилни киселини, лекарствени средства които ги съдържат, тяхното приложение и получаване |
| NO20020374A NO20020374D0 (no) | 1999-07-27 | 2002-01-24 | Karboksylsyreamider, medikamenter inneholdende disse forbindelser, deres anvendelse og fremstilling |
| ZA200200694A ZA200200694B (en) | 1999-07-27 | 2002-01-25 | Carboxylic acid amides, medicaments containing these compounds and the use and production thereof. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19935219A DE19935219A1 (de) | 1999-07-27 | 1999-07-27 | Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19935219A1 true DE19935219A1 (de) | 2001-02-01 |
Family
ID=7916195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19935219A Withdrawn DE19935219A1 (de) | 1999-07-27 | 1999-07-27 | Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US6362210B1 (enExample) |
| EP (1) | EP1261321A2 (enExample) |
| JP (1) | JP5010788B2 (enExample) |
| KR (1) | KR20020032537A (enExample) |
| CN (1) | CN1414849A (enExample) |
| AR (1) | AR024944A1 (enExample) |
| AU (1) | AU6436800A (enExample) |
| BG (1) | BG106343A (enExample) |
| BR (1) | BR0013184A (enExample) |
| CA (1) | CA2378382C (enExample) |
| CO (1) | CO5180639A1 (enExample) |
| CZ (1) | CZ2002313A3 (enExample) |
| DE (1) | DE19935219A1 (enExample) |
| EA (1) | EA200200114A1 (enExample) |
| EE (1) | EE200200041A (enExample) |
| HR (1) | HRP20020072A2 (enExample) |
| HU (1) | HUP0204373A3 (enExample) |
| IL (1) | IL147707A0 (enExample) |
| MX (1) | MXPA02000822A (enExample) |
| NO (1) | NO20020374D0 (enExample) |
| PL (1) | PL361335A1 (enExample) |
| SK (1) | SK2962002A3 (enExample) |
| TR (1) | TR200200226T2 (enExample) |
| UY (1) | UY26256A1 (enExample) |
| WO (1) | WO2001007020A2 (enExample) |
| YU (1) | YU5502A (enExample) |
| ZA (1) | ZA200200694B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2825090A1 (fr) * | 2001-05-28 | 2002-11-29 | Aventis Pharma Sa | Derives chimiques et leur application comme agent antitelomerase |
| WO2002096903A3 (fr) * | 2001-05-28 | 2003-04-17 | Aventis Pharma Sa | Derives chimiques et leur application comme agent antitelomerase |
| US7482352B2 (en) | 2001-03-23 | 2009-01-27 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agents |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6645964B1 (en) * | 1999-11-29 | 2003-11-11 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agent |
| EP1319657A4 (en) * | 2000-09-22 | 2005-03-02 | Nihon Nohyaku Co Ltd | N- (4-PYRAZOLYL AMIDE) DERIVATIVES, CHEMICALS FOR AGRICULTURAL AND HORTICULTURAL USE AND APPLICATIONS THEREOF |
| DE10065042A1 (de) * | 2000-12-23 | 2002-06-27 | Boehringer Ingelheim Pharma | Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
| CA2441274A1 (en) * | 2001-04-18 | 2002-10-24 | Pharmacia Italia S.P.A. | Aurones as telomerase inhibitors |
| GB0127615D0 (en) * | 2001-07-09 | 2002-01-09 | Aventis Pharm Prod Inc | Substituted amides, sulfonamides and ureas useful for inhibiting kinase activity |
| CA2468544A1 (en) * | 2001-12-10 | 2003-06-19 | Amgen Inc. | Vanilloid receptor ligands |
| US20070232572A1 (en) * | 2003-02-07 | 2007-10-04 | Aventis Pharma S.A. | Chemical derivatives as antitelomerase agents which bind specifically to the G-quadruplex DNA structures and their application as a specific anticancer agent |
| AU2004222626B2 (en) * | 2003-03-21 | 2010-06-24 | H. Lundbeck A/S | Substituted p-diaminobenzene derivatives |
| GB0316546D0 (en) * | 2003-07-15 | 2003-08-20 | Novartis Ag | Process for the manufacture of organic compounds |
| MX2007003342A (es) * | 2004-09-21 | 2007-06-05 | Synta Pharmaceutical Corp | Compuestos para inflamacion y usos relacionados con trastornos inmunitarios. |
| US8084492B2 (en) * | 2004-11-19 | 2011-12-27 | The New Industry Research Organization | Benzofuran compound and pharmaceutical composition containing the same |
| US20070072873A1 (en) * | 2005-09-27 | 2007-03-29 | Henrietta Dehmlow | Novel thiophene derivatives which are HM74A agonists |
| PT2799427T (pt) | 2006-07-05 | 2018-10-16 | Fibrotech Therapeutics Pty Ltd | Compostos terapêuticos |
| NZ601866A (en) | 2007-06-29 | 2013-12-20 | Acucela Inc | Alkynyl phenyl derivative compounds for treating ophthalmic diseases and disorders |
| WO2009014150A1 (ja) | 2007-07-24 | 2009-01-29 | Astellas Pharma Inc. | ベンズイミダゾール誘導体 |
| KR101593708B1 (ko) * | 2007-12-21 | 2016-02-12 | 피브로테크 세라퓨틱 피티와이 엘티디 | 항섬유증 제제의 할로겐화 유사체 |
| US20110054034A1 (en) * | 2008-02-08 | 2011-03-03 | Schroeder Jr William | Methods of using carboxylic amides as antimicrobial agents |
| US20110282066A1 (en) | 2009-01-27 | 2011-11-17 | Takashi Furutani | Screening method for substance useful as agent for treating prostate cancer |
| WO2010144959A1 (en) * | 2009-06-18 | 2010-12-23 | Fibrotech Therapeutics Pty Ltd | Analogues of anti-fibrotic agents |
| EP2491030B1 (en) | 2009-10-22 | 2015-07-15 | Fibrotech Therapeutics PTY LTD | Fused ring analogues of anti-fibrotic agents |
| EP2758041B1 (de) | 2011-09-20 | 2021-01-13 | Basf Se | Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung |
| EP2794569B1 (en) * | 2011-12-21 | 2017-05-10 | Biota Europe Ltd | Heterocyclic urea compounds |
| CA3052036A1 (en) | 2017-02-03 | 2018-08-09 | Certa Therapeutics Pty Ltd. | Anti-fibrotic compounds |
| CN110357789B (zh) * | 2018-04-11 | 2022-09-30 | 华东理工大学 | 作为dhodh抑制剂的n-取代丙烯酰胺衍生物及其制备和用途 |
| CN114831977B (zh) * | 2021-02-02 | 2023-12-19 | 北京大学 | 苯甲酸类衍生物作为trpm2蛋白抑制剂的用途 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5640710B2 (enExample) * | 1973-01-18 | 1981-09-22 | ||
| JPS5848545B2 (ja) * | 1974-04-18 | 1983-10-28 | キツセイヤクヒンコウギヨウ カブシキガイシヤ | シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウ |
| JPS6097946A (ja) * | 1983-11-01 | 1985-05-31 | Ono Pharmaceut Co Ltd | カルボキサミド誘導体 |
| JPS60139646A (ja) * | 1983-12-27 | 1985-07-24 | Otsuka Pharmaceut Factory Inc | ナフタレン誘導体 |
| JPS60146855A (ja) * | 1984-01-11 | 1985-08-02 | Ono Pharmaceut Co Ltd | アニリン誘導体 |
| JPS61170528A (ja) | 1985-01-22 | 1986-08-01 | Sutaaroi Sangyo Kk | コバルトの剥離回収方法 |
| US5239083A (en) * | 1991-03-11 | 1993-08-24 | Kyowa Hakko Kogyo Co., Ltd. | Indole derivatives which inhibit steroid 5α reductase |
| JPH0578315A (ja) * | 1991-03-11 | 1993-03-30 | Kyowa Hakko Kogyo Co Ltd | インドール誘導体 |
| JPH0672866A (ja) * | 1992-07-02 | 1994-03-15 | Chugoku Igakuka Gakuin Yakubutsu Kenkyusho | 分化誘導剤 |
| IT1276462B1 (it) | 1995-07-03 | 1997-10-31 | Rotta Research Lab | Diamidi aromatiche acide ad attivita' antigastrinica, procedimento per la loro preparazione e loro uso farmaceutico |
| JPH09154575A (ja) * | 1995-10-04 | 1997-06-17 | Soosei:Kk | テロメラーゼ |
| IT1286141B1 (it) | 1996-07-02 | 1998-07-07 | Rotta Research Lab | Derivati diammidici dell'acido antranilico ad attivita' antigastrinica procedimento per la loro preparazione e loro uso farmaceutico. |
| FR2759368B1 (fr) | 1997-02-10 | 2001-06-01 | Galderma Rech Dermatologique | Composes biaromatiques, compositions les contenant et utilisations |
| JPH1149676A (ja) * | 1997-07-31 | 1999-02-23 | Geron Corp | ピリジン系テロメラーゼ阻害剤 |
| EP1003712A1 (en) * | 1997-08-05 | 2000-05-31 | American Home Products Corporation | Anthranilic acid analogs |
| EP1037880B1 (en) | 1997-12-11 | 2004-06-30 | Janssen Pharmaceutica N.V. | Retinoic acid mimetic anilides |
| CA2338804A1 (en) | 1998-07-28 | 2000-02-10 | Smithkline Beecham Corporation | Propenamides as ccr5 modulators |
| AU1707700A (en) | 1998-10-29 | 2000-05-22 | Bristol-Myers Squibb Company | Novel inhibitors of impdh enzyme |
-
1999
- 1999-07-27 DE DE19935219A patent/DE19935219A1/de not_active Withdrawn
-
2000
- 2000-07-18 US US09/618,702 patent/US6362210B1/en not_active Expired - Lifetime
- 2000-07-22 MX MXPA02000822A patent/MXPA02000822A/es unknown
- 2000-07-22 EP EP00951431A patent/EP1261321A2/de not_active Withdrawn
- 2000-07-22 SK SK296-2002A patent/SK2962002A3/sk not_active Application Discontinuation
- 2000-07-22 CN CN00812829A patent/CN1414849A/zh active Pending
- 2000-07-22 EE EEP200200041A patent/EE200200041A/xx unknown
- 2000-07-22 EA EA200200114A patent/EA200200114A1/ru unknown
- 2000-07-22 HU HU0204373A patent/HUP0204373A3/hu unknown
- 2000-07-22 HR HR20020072A patent/HRP20020072A2/hr not_active Application Discontinuation
- 2000-07-22 CA CA002378382A patent/CA2378382C/en not_active Expired - Fee Related
- 2000-07-22 KR KR1020027001103A patent/KR20020032537A/ko not_active Withdrawn
- 2000-07-22 TR TR2002/00226T patent/TR200200226T2/xx unknown
- 2000-07-22 JP JP2001511906A patent/JP5010788B2/ja not_active Expired - Fee Related
- 2000-07-22 BR BR0013184-9A patent/BR0013184A/pt not_active IP Right Cessation
- 2000-07-22 CZ CZ2002313A patent/CZ2002313A3/cs unknown
- 2000-07-22 AU AU64368/00A patent/AU6436800A/en not_active Abandoned
- 2000-07-22 IL IL14770700A patent/IL147707A0/xx unknown
- 2000-07-22 WO PCT/EP2000/007057 patent/WO2001007020A2/de not_active Ceased
- 2000-07-22 PL PL36133500A patent/PL361335A1/xx not_active Application Discontinuation
- 2000-07-22 YU YU5502A patent/YU5502A/sh unknown
- 2000-07-25 UY UY26256A patent/UY26256A1/es not_active Application Discontinuation
- 2000-07-26 AR ARP000103858A patent/AR024944A1/es not_active Application Discontinuation
- 2000-07-27 CO CO00056547A patent/CO5180639A1/es not_active Application Discontinuation
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2002
- 2002-01-03 US US10/037,555 patent/US6727250B2/en not_active Expired - Lifetime
- 2002-01-23 BG BG106343A patent/BG106343A/xx unknown
- 2002-01-24 NO NO20020374A patent/NO20020374D0/no not_active Application Discontinuation
- 2002-01-25 ZA ZA200200694A patent/ZA200200694B/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7482352B2 (en) | 2001-03-23 | 2009-01-27 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agents |
| FR2825090A1 (fr) * | 2001-05-28 | 2002-11-29 | Aventis Pharma Sa | Derives chimiques et leur application comme agent antitelomerase |
| WO2002096903A3 (fr) * | 2001-05-28 | 2003-04-17 | Aventis Pharma Sa | Derives chimiques et leur application comme agent antitelomerase |
| US6995175B2 (en) | 2001-05-28 | 2006-02-07 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agent |
Also Published As
| Publication number | Publication date |
|---|---|
| US6727250B2 (en) | 2004-04-27 |
| HUP0204373A2 (hu) | 2003-03-28 |
| CO5180639A1 (es) | 2002-07-30 |
| JP5010788B2 (ja) | 2012-08-29 |
| ZA200200694B (en) | 2003-09-23 |
| HUP0204373A3 (en) | 2004-12-28 |
| HRP20020072A2 (en) | 2003-10-31 |
| IL147707A0 (en) | 2002-08-14 |
| WO2001007020A2 (de) | 2001-02-01 |
| PL361335A1 (en) | 2004-10-04 |
| CZ2002313A3 (cs) | 2002-06-12 |
| EE200200041A (et) | 2003-04-15 |
| NO20020374L (no) | 2002-01-24 |
| US6362210B1 (en) | 2002-03-26 |
| AR024944A1 (es) | 2002-10-30 |
| MXPA02000822A (es) | 2002-10-23 |
| BR0013184A (pt) | 2003-07-01 |
| UY26256A1 (es) | 2001-03-16 |
| KR20020032537A (ko) | 2002-05-03 |
| CA2378382A1 (en) | 2001-02-01 |
| JP2003518475A (ja) | 2003-06-10 |
| SK2962002A3 (en) | 2002-06-04 |
| CA2378382C (en) | 2008-09-23 |
| NO20020374D0 (no) | 2002-01-24 |
| EA200200114A1 (ru) | 2002-12-26 |
| YU5502A (sh) | 2005-06-10 |
| WO2001007020A3 (de) | 2002-09-19 |
| EP1261321A2 (de) | 2002-12-04 |
| CN1414849A (zh) | 2003-04-30 |
| TR200200226T2 (tr) | 2002-09-23 |
| BG106343A (bg) | 2002-08-30 |
| US20020099089A1 (en) | 2002-07-25 |
| AU6436800A (en) | 2001-02-13 |
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