SK7032003A3 - Substituted pyrroloquinolines and pyridoquinolines as serotonin agonists and antagonists - Google Patents
Substituted pyrroloquinolines and pyridoquinolines as serotonin agonists and antagonists Download PDFInfo
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- SK7032003A3 SK7032003A3 SK703-2003A SK7032003A SK7032003A3 SK 7032003 A3 SK7032003 A3 SK 7032003A3 SK 7032003 A SK7032003 A SK 7032003A SK 7032003 A3 SK7032003 A3 SK 7032003A3
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- Slovakia
- Prior art keywords
- phenyl
- substituted
- alkyl
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- 239000003420 antiserotonin agent Substances 0.000 title abstract description 6
- 239000000952 serotonin receptor agonist Substances 0.000 title abstract description 5
- OZKOMUDCMCEDTM-UHFFFAOYSA-N 1,7-phenanthroline Chemical class C1=CC=C2C3=NC=CC=C3C=CC2=N1 OZKOMUDCMCEDTM-UHFFFAOYSA-N 0.000 title 1
- SLHCMPVPVQSTBV-UHFFFAOYSA-N C1=CNC2=C3C=CN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=CN=C3C=CC2=C1 SLHCMPVPVQSTBV-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 163
- 150000003839 salts Chemical group 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- -1 ethylenedioxy Chemical group 0.000 claims description 563
- 229910052739 hydrogen Inorganic materials 0.000 claims description 351
- 125000000217 alkyl group Chemical group 0.000 claims description 332
- 239000001257 hydrogen Substances 0.000 claims description 330
- 150000002431 hydrogen Chemical class 0.000 claims description 291
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical group CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims description 257
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 172
- 125000003342 alkenyl group Chemical group 0.000 claims description 170
- 125000000304 alkynyl group Chemical group 0.000 claims description 150
- VEAUDLLZYJVHRI-UHFFFAOYSA-N Trichlormethine Chemical compound Cl.ClCCN(CCCl)CCCl VEAUDLLZYJVHRI-UHFFFAOYSA-N 0.000 claims description 145
- 229910052760 oxygen Inorganic materials 0.000 claims description 142
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 141
- 125000005842 heteroatom Chemical group 0.000 claims description 136
- 229910052736 halogen Inorganic materials 0.000 claims description 135
- 150000002367 halogens Chemical class 0.000 claims description 135
- 229910052757 nitrogen Inorganic materials 0.000 claims description 133
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 129
- 125000003545 alkoxy group Chemical group 0.000 claims description 122
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 120
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 117
- PCPQWYHRMVULIX-UHFFFAOYSA-P [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;dinitrate Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 PCPQWYHRMVULIX-UHFFFAOYSA-P 0.000 claims description 116
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 116
- 125000003118 aryl group Chemical group 0.000 claims description 113
- 239000001301 oxygen Chemical group 0.000 claims description 108
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 107
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 107
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 106
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 106
- 125000000623 heterocyclic group Chemical group 0.000 claims description 103
- 125000004434 sulfur atom Chemical group 0.000 claims description 102
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 77
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 71
- OMJKVIFSWSQTGQ-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)quinazoline-5,8-dione Chemical group C1CN1C=1C(=O)C2=NC=NC=C2C(=O)C=1N1CC1 OMJKVIFSWSQTGQ-UHFFFAOYSA-N 0.000 claims description 70
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 67
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 65
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 54
- 229910052717 sulfur Inorganic materials 0.000 claims description 52
- 125000001188 haloalkyl group Chemical group 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 47
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 46
- 125000002837 carbocyclic group Chemical group 0.000 claims description 43
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 43
- BTIIGNUPPKUQAP-UHFFFAOYSA-N [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;diperchlorate Chemical group [O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 BTIIGNUPPKUQAP-UHFFFAOYSA-N 0.000 claims description 40
- 239000000460 chlorine Substances 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 35
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
- 239000011737 fluorine Substances 0.000 claims description 33
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 30
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 29
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 28
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 125000004414 alkyl thio group Chemical group 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 23
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 20
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 230000017105 transposition Effects 0.000 claims description 9
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 8
- 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 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 6
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 6
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 6
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 5
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
- FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 claims description 5
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 5
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 5
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 5
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 5
- 125000005917 3-methylpentyl group Chemical group 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- RMAINTGPKFNBDP-UHFFFAOYSA-N 2-methylphenol Chemical group [CH2]C1=CC=CC=C1O RMAINTGPKFNBDP-UHFFFAOYSA-N 0.000 claims description 4
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 101150065749 Churc1 gene Proteins 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 2
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 2
- 125000004345 1-phenyl-2-propyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000005807 2,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C([H])C(=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- 125000006188 2-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 2
- 230000004075 alteration Effects 0.000 claims description 2
- 125000004125 inden-2-yl group Chemical group [H]C1=C(*)C([H])([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 12
- 125000004965 chloroalkyl group Chemical group 0.000 claims 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 10
- 201000000980 schizophrenia Diseases 0.000 abstract description 10
- 239000000203 mixture Substances 0.000 abstract description 9
- 208000019901 Anxiety disease Diseases 0.000 abstract description 8
- 230000036506 anxiety Effects 0.000 abstract description 8
- 208000035475 disorder Diseases 0.000 abstract description 8
- 208000008589 Obesity Diseases 0.000 abstract description 7
- 235000020824 obesity Nutrition 0.000 abstract description 7
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- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 239000002400 serotonin 2A antagonist Substances 0.000 description 1
- 230000009329 sexual behaviour Effects 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 230000036263 tachygastria Effects 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- AGZPNUZBDCYTBB-UHFFFAOYSA-N triethyl methanetricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)OCC AGZPNUZBDCYTBB-UHFFFAOYSA-N 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- BNOIMFITGLLJTH-UHFFFAOYSA-N trimethyl methanetricarboxylate Chemical group COC(=O)C(C(=O)OC)C(=O)OC BNOIMFITGLLJTH-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/16—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- C07D498/12—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 three hetero rings
- C07D498/16—Peri-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25674500P | 2000-12-20 | 2000-12-20 | |
| PCT/US2001/049380 WO2002059124A2 (fr) | 2000-12-20 | 2001-12-19 | Pyrroloquinoleines et pyridoquinoleines substituees comme agonistes et antagonistes de la serotonine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK7032003A3 true SK7032003A3 (en) | 2004-04-06 |
Family
ID=22973430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK703-2003A SK7032003A3 (en) | 2000-12-20 | 2001-12-19 | Substituted pyrroloquinolines and pyridoquinolines as serotonin agonists and antagonists |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6777406B2 (fr) |
| EP (1) | EP1399445B9 (fr) |
| JP (1) | JP4386639B2 (fr) |
| KR (1) | KR20030070590A (fr) |
| AT (1) | ATE438646T1 (fr) |
| AU (1) | AU2002246726B2 (fr) |
| BG (1) | BG107863A (fr) |
| BR (1) | BR0116348A (fr) |
| CA (1) | CA2432181C (fr) |
| CZ (1) | CZ20031707A3 (fr) |
| DE (1) | DE60139511D1 (fr) |
| EE (1) | EE200300303A (fr) |
| ES (1) | ES2329553T4 (fr) |
| HU (1) | HUP0303530A3 (fr) |
| IL (1) | IL156261A0 (fr) |
| IS (1) | IS6851A (fr) |
| MX (1) | MXPA03005355A (fr) |
| NO (1) | NO20032798L (fr) |
| PL (1) | PL366627A1 (fr) |
| RU (1) | RU2003121306A (fr) |
| SK (1) | SK7032003A3 (fr) |
| WO (1) | WO2002059124A2 (fr) |
| ZA (1) | ZA200304304B (fr) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR031200A1 (es) | 2000-11-03 | 2003-09-10 | Wyeth Corp | Cicloocta [b] [1,4] diazepino [6,7,1-hi] indoles y derivados |
| US6858604B2 (en) | 2000-11-03 | 2005-02-22 | Wyeth | Cyclohepta[b][1,4]diazepino[6,7,1-hi]indoles and derivatives |
| AR031202A1 (es) | 2000-11-03 | 2003-09-10 | Wyeth Corp | Ciclopenta(b) (1,4)diazepino(6,7,1-hi) indoles y derivados |
| TW200307540A (en) | 2002-04-25 | 2003-12-16 | Wyeth Corp | [1, 4]Diazocino[7, 8, 1-hi] indole derivatives as antipsychotic and antiobesity agents |
| TWI312781B (en) | 2002-04-25 | 2009-08-01 | [1,4]diazepino[6,7,1-ij]quinoline derivatives as antipsychotic and antiobesity agents | |
| TW200307682A (en) | 2002-04-25 | 2003-12-16 | Wyeth Corp | 1,2,3,4,7,8-Hexahydro-6H-[1,4]diazepino[6,7,1-ij]quinoline derivatives as antipsychotic and antiobesity agents |
| CL2004000826A1 (es) | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
| EP2248524A3 (fr) | 2004-08-25 | 2011-03-09 | Takeda Pharmaceutical Company Limited | Agents preventifs/remedes pour l'incontinence de stress et procede de selecetion de ceux-ci |
| US20070021612A1 (en) * | 2004-11-04 | 2007-01-25 | University Of Notre Dame Du Lac | Processes and compounds for preparing histone deacetylase inhibitors and intermediates thereof |
| US7235688B1 (en) | 2004-11-04 | 2007-06-26 | University Of Notre Dame Du Lac | Process for preparing histone deacetylase inhibitors and intermediates thereof |
| GT200500317A (es) * | 2004-11-05 | 2006-10-27 | Proceso para preparar compuestos de quinolina y productos obtenidos de los mismos | |
| AR054849A1 (es) * | 2005-07-26 | 2007-07-18 | Wyeth Corp | Diazepinoquinolinas, sintesis de las mismas, e intermediarios para obtenerlas |
| TW200734334A (en) * | 2006-01-13 | 2007-09-16 | Wyeth Corp | Treatment of substance abuse |
| JP2009531434A (ja) * | 2006-03-24 | 2009-09-03 | ワイス | 痛みの治療 |
| CN101410112A (zh) * | 2006-03-24 | 2009-04-15 | 惠氏公司 | 治疗抑郁症的新治疗组合 |
| EP2742936A1 (fr) | 2006-05-16 | 2014-06-18 | Takeda Pharmaceutical Company Limited | Composé hétérocyclique condensé et son utilisation |
| CL2008002777A1 (es) * | 2007-09-21 | 2010-01-22 | Wyeth Corp | Metodo de preparacion de compuestos diazepinoquinolinicos quirales por recristalizacion en un sistema de solvente ternario. |
| US20100266504A1 (en) | 2007-11-15 | 2010-10-21 | Takahiro Matsumoto | Condensed pyridine derivative and use thereof |
| AU2010303270A1 (en) | 2009-10-09 | 2012-05-03 | Zafgen Corporation | Sulphone compounds for use in the treatment of obesity |
| EP2510949A4 (fr) | 2009-12-11 | 2013-11-13 | Astellas Pharma Inc | Agent thérapeutique pour la fibromyalgie |
| BR112013001613A2 (pt) * | 2010-07-22 | 2016-05-24 | Zafgen Inc | compostos tricíclicos e métodos para fazer e usar os mesmos. |
| US9321740B2 (en) | 2011-01-26 | 2016-04-26 | Zafgen, Inc. | Tetrazole compounds and methods of making and using same |
| BR112013028665A2 (pt) | 2011-05-06 | 2016-09-06 | Zafgen Inc | compostos de sulfonamida tricíclicos e métodos para fazer e usar os mesmos |
| MX343688B (es) | 2011-05-06 | 2016-11-16 | Zafgen Inc | Compuestos tricíclicos de sulfonamida y pirazolo y métodos para su fabricación y uso. |
| KR101979039B1 (ko) | 2011-05-06 | 2019-05-15 | 자프겐 인크. | 부분 포화된 삼환식 화합물 및 그리고 그의 제조방법 및 그를 이용하는 방법 |
| US9440943B2 (en) | 2012-01-18 | 2016-09-13 | Zafgen, Inc. | Tricyclic sulfone compounds and methods of making and using same |
| JP6035347B2 (ja) | 2012-01-18 | 2016-11-30 | ザフゲン，インコーポレイテッド | 三環式スルホンアミド化合物ならびにその作製および使用方法 |
| KR20150080614A (ko) | 2012-11-05 | 2015-07-09 | 자프겐 인크. | 비만의 치료 및/또는 제어에서 사용하기 위한 트리시클릭 화합물 |
| NZ707773A (en) | 2012-11-05 | 2019-05-31 | Zafgen Inc | Methods of treating liver diseases |
| MX2015005732A (es) | 2012-11-05 | 2015-12-16 | Zafgen Inc | Compuestos tricíclicos y métodos para hacer y utilizar los mismos. |
| EP2919788A4 (fr) | 2012-11-14 | 2016-05-25 | Univ Johns Hopkins | Méthodes et compositions pour le traitement de la schizophrénie |
| EP2981266B1 (fr) * | 2013-03-04 | 2018-01-03 | Daya CNS LLC | Dérivés de pyridoindolobenz[b,d]azépines pentacycliques et leurs utilisations |
| WO2015066344A1 (fr) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | Agonistes du récepteur 5-ht2c et compositions et procédés d'utilisation |
| EP3733204A4 (fr) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | Agent thérapeutique pour incontinence urinaire de stress et incontinence fécale |
| CN109897039B (zh) * | 2019-03-13 | 2021-03-30 | 中国科学院化学研究所 | 一种制备吡咯并[3,2,1-ij]喹啉酮化合物的方法 |
| US20240208973A1 (en) * | 2021-04-13 | 2024-06-27 | The Regents Of The University Of California | Tetracyclic compounds for treating brain disorders |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013652A (en) | 1972-06-19 | 1977-03-22 | Endo Laboratories, Inc. | Pyridopyrrolobenzoxazine |
| US4238607A (en) | 1972-06-19 | 1980-12-09 | Endo Laboratories Inc. | Pyridopyrrolo benzheterocycles |
| US3914421A (en) | 1972-06-19 | 1975-10-21 | Endo Lab | Pyridopyrrolobenzheterocycles for combatting depression |
| US4115577A (en) | 1972-06-19 | 1978-09-19 | Endo Laboratories, Inc. | Pyridopyrrolobenzheterocycles |
| US4183936A (en) | 1972-06-19 | 1980-01-15 | Endo Laboratories, Inc. | Pyridopyrrolobenzheterocycles |
| US4219550A (en) | 1978-11-09 | 1980-08-26 | E. I. Du Pont De Nemours And Company | Cis- and trans- octahydropyridopyrrolobenzheterocycles |
| HUT61548A (en) * | 1990-08-27 | 1993-01-28 | Sandoz Ag | Process for producing indolonaphthyridine derivatives and pharmaceutical compositions comprising such compounds |
-
2001
- 2001-12-19 IL IL15626101A patent/IL156261A0/xx unknown
- 2001-12-19 KR KR10-2003-7008267A patent/KR20030070590A/ko not_active Application Discontinuation
- 2001-12-19 AU AU2002246726A patent/AU2002246726B2/en not_active Ceased
- 2001-12-19 ES ES01994318T patent/ES2329553T4/es not_active Expired - Lifetime
- 2001-12-19 AT AT01994318T patent/ATE438646T1/de not_active IP Right Cessation
- 2001-12-19 EE EEP200300303A patent/EE200300303A/xx unknown
- 2001-12-19 HU HU0303530A patent/HUP0303530A3/hu unknown
- 2001-12-19 RU RU2003121306/04A patent/RU2003121306A/ru not_active Application Discontinuation
- 2001-12-19 MX MXPA03005355A patent/MXPA03005355A/es unknown
- 2001-12-19 CA CA002432181A patent/CA2432181C/fr not_active Expired - Fee Related
- 2001-12-19 PL PL01366627A patent/PL366627A1/xx unknown
- 2001-12-19 DE DE60139511T patent/DE60139511D1/de not_active Expired - Lifetime
- 2001-12-19 CZ CZ20031707A patent/CZ20031707A3/cs unknown
- 2001-12-19 WO PCT/US2001/049380 patent/WO2002059124A2/fr active IP Right Grant
- 2001-12-19 SK SK703-2003A patent/SK7032003A3/sk unknown
- 2001-12-19 US US10/026,993 patent/US6777406B2/en not_active Expired - Lifetime
- 2001-12-19 BR BR0116348-5A patent/BR0116348A/pt not_active Application Discontinuation
- 2001-12-19 EP EP01994318A patent/EP1399445B9/fr not_active Expired - Lifetime
- 2001-12-19 JP JP2002559426A patent/JP4386639B2/ja not_active Expired - Fee Related
-
2003
- 2003-05-30 BG BG107863A patent/BG107863A/xx unknown
- 2003-06-02 ZA ZA200304304A patent/ZA200304304B/en unknown
- 2003-06-18 IS IS6851A patent/IS6851A/is unknown
- 2003-06-19 NO NO20032798A patent/NO20032798L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20040092502A1 (en) | 2004-05-13 |
| KR20030070590A (ko) | 2003-08-30 |
| CA2432181C (fr) | 2009-11-17 |
| JP4386639B2 (ja) | 2009-12-16 |
| EP1399445B1 (fr) | 2009-08-05 |
| HUP0303530A3 (en) | 2012-10-29 |
| NO20032798D0 (no) | 2003-06-19 |
| MXPA03005355A (es) | 2004-05-27 |
| IL156261A0 (en) | 2004-01-04 |
| ES2329553T4 (es) | 2010-12-07 |
| CA2432181A1 (fr) | 2002-08-01 |
| NO20032798L (no) | 2003-08-19 |
| DE60139511D1 (de) | 2009-09-17 |
| RU2003121306A (ru) | 2005-03-10 |
| ZA200304304B (en) | 2004-09-02 |
| HUP0303530A2 (hu) | 2004-01-28 |
| EE200300303A (et) | 2003-12-15 |
| PL366627A1 (en) | 2005-02-07 |
| WO2002059124A3 (fr) | 2004-01-08 |
| CZ20031707A3 (cs) | 2003-11-12 |
| EP1399445A2 (fr) | 2004-03-24 |
| BG107863A (en) | 2004-06-30 |
| EP1399445B9 (fr) | 2010-07-21 |
| IS6851A (is) | 2003-06-18 |
| ES2329553T3 (es) | 2009-11-27 |
| BR0116348A (pt) | 2004-11-23 |
| JP2004528290A (ja) | 2004-09-16 |
| AU2002246726B2 (en) | 2007-03-01 |
| ATE438646T1 (de) | 2009-08-15 |
| US6777406B2 (en) | 2004-08-17 |
| WO2002059124A2 (fr) | 2002-08-01 |
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