MXPA05003950A - Compuestos inhibidores de la integrasa triciclicos preorganizados. - Google Patents
Compuestos inhibidores de la integrasa triciclicos preorganizados.Info
- Publication number
- MXPA05003950A MXPA05003950A MXPA05003950A MXPA05003950A MXPA05003950A MX PA05003950 A MXPA05003950 A MX PA05003950A MX PA05003950 A MXPA05003950 A MX PA05003950A MX PA05003950 A MXPA05003950 A MX PA05003950A MX PA05003950 A MXPA05003950 A MX PA05003950A
- Authority
- MX
- Mexico
- Prior art keywords
- phosphonate
- substituted
- compound
- compound according
- aryl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 294
- 229940124524 integrase inhibitor Drugs 0.000 title description 5
- 239000002850 integrase inhibitor Substances 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 277
- 229940002612 prodrug Drugs 0.000 claims abstract description 104
- 239000000651 prodrug Substances 0.000 claims abstract description 104
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 79
- 125000003118 aryl group Chemical group 0.000 claims abstract description 69
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 65
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 38
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 36
- 125000001424 substituent group Chemical group 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 108010002459 HIV Integrase Proteins 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 436
- -1 polyethyleneoxy Polymers 0.000 claims description 251
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 209
- 239000000203 mixture Substances 0.000 claims description 102
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 97
- 238000002360 preparation method Methods 0.000 claims description 82
- 150000001412 amines Chemical class 0.000 claims description 66
- 150000002148 esters Chemical class 0.000 claims description 56
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 125000006239 protecting group Chemical group 0.000 claims description 37
- 239000003153 chemical reaction reagent Substances 0.000 claims description 36
- 125000002947 alkylene group Chemical group 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 27
- 229910019142 PO4 Inorganic materials 0.000 claims description 26
- 239000010452 phosphate Substances 0.000 claims description 25
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000003112 inhibitor Substances 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 150000003951 lactams Chemical group 0.000 claims description 15
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 claims description 15
- 239000002243 precursor Substances 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000004419 alkynylene group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 10
- 102100034343 Integrase Human genes 0.000 claims description 10
- 150000007942 carboxylates Chemical class 0.000 claims description 10
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 230000003834 intracellular effect Effects 0.000 claims description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 150000002596 lactones Chemical group 0.000 claims description 9
- 208000030507 AIDS Diseases 0.000 claims description 8
- 208000031886 HIV Infections Diseases 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 150000001350 alkyl halides Chemical class 0.000 claims description 8
- 150000001356 alkyl thiols Chemical class 0.000 claims description 8
- 239000002207 metabolite Substances 0.000 claims description 8
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 7
- 239000002777 nucleoside Substances 0.000 claims description 7
- 125000003835 nucleoside group Chemical group 0.000 claims description 7
- 229960002317 succinimide Drugs 0.000 claims description 7
- 125000003003 spiro group Chemical group 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 6
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 5
- 208000037357 HIV infectious disease Diseases 0.000 claims description 4
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 4
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
- 229940099797 HIV integrase inhibitor Drugs 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000004599 antimicrobial Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 239000003084 hiv integrase inhibitor Substances 0.000 claims description 3
- 239000002955 immunomodulating agent Substances 0.000 claims description 3
- 229940121354 immunomodulator Drugs 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 230000008685 targeting Effects 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 229960005475 antiinfective agent Drugs 0.000 claims description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 230000002584 immunomodulator Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 210000000265 leukocyte Anatomy 0.000 claims 5
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical group CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 claims 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims 1
- 101100193519 Caenorhabditis elegans qui-1 gene Proteins 0.000 claims 1
- 108010010369 HIV Protease Proteins 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 103
- 239000000543 intermediate Substances 0.000 abstract description 40
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 125000006413 ring segment Chemical group 0.000 abstract description 7
- 150000002829 nitrogen Chemical class 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 263
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 135
- 239000000243 solution Substances 0.000 description 112
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 104
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 83
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 76
- 230000000875 corresponding effect Effects 0.000 description 72
- 238000010511 deprotection reaction Methods 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 52
- 239000002585 base Substances 0.000 description 51
- 238000005481 NMR spectroscopy Methods 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 44
- 229920006395 saturated elastomer Polymers 0.000 description 44
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
- 235000019439 ethyl acetate Nutrition 0.000 description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 33
- 238000009472 formulation Methods 0.000 description 33
- 125000003710 aryl alkyl group Chemical group 0.000 description 32
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
- 239000007787 solid Substances 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000004480 active ingredient Substances 0.000 description 30
- 150000001408 amides Chemical class 0.000 description 30
- 150000005690 diesters Chemical class 0.000 description 30
- 239000007858 starting material Substances 0.000 description 28
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 26
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 26
- 125000004122 cyclic group Chemical group 0.000 description 25
- 239000002253 acid Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 241000725303 Human immunodeficiency virus Species 0.000 description 23
- 239000003814 drug Substances 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 20
- 238000005859 coupling reaction Methods 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 20
- 239000011734 sodium Substances 0.000 description 20
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 19
- 125000002015 acyclic group Chemical group 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 19
- 229940079593 drug Drugs 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 19
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- 229940059260 amidate Drugs 0.000 description 18
- 238000006460 hydrolysis reaction Methods 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 230000007062 hydrolysis Effects 0.000 description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 16
- 235000021317 phosphate Nutrition 0.000 description 16
- 150000003009 phosphonic acids Chemical class 0.000 description 16
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 15
- 150000001299 aldehydes Chemical class 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 150000002440 hydroxy compounds Chemical class 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 14
- 235000011181 potassium carbonates Nutrition 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
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- 150000002989 phenols Chemical class 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 230000000840 anti-viral effect Effects 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 11
- 239000003495 polar organic solvent Substances 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
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- 239000012043 crude product Substances 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
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- 239000012442 inert solvent Substances 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- 229910052698 phosphorus Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000005804 alkylation reaction Methods 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 9
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
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- 230000009467 reduction Effects 0.000 description 9
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 125000005997 bromomethyl group Chemical group 0.000 description 8
- 125000004185 ester group Chemical group 0.000 description 8
- ROBXZHNBBCHEIQ-BYPYZUCNSA-N ethyl (2s)-2-aminopropanoate Chemical compound CCOC(=O)[C@H](C)N ROBXZHNBBCHEIQ-BYPYZUCNSA-N 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 125000005647 linker group Chemical group 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000012279 sodium borohydride Substances 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- 238000000844 transformation Methods 0.000 description 8
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
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- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C07D498/20—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41896302P | 2002-10-16 | 2002-10-16 | |
| US47878303P | 2003-06-16 | 2003-06-16 | |
| PCT/US2003/032666 WO2004035576A2 (en) | 2002-10-16 | 2003-10-16 | Pre-organized tricyclic integrase inhibitor compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05003950A true MXPA05003950A (es) | 2005-06-17 |
Family
ID=32110203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA05003950A MXPA05003950A (es) | 2002-10-16 | 2003-10-16 | Compuestos inhibidores de la integrasa triciclicos preorganizados. |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US20040157804A1 (enExample) |
| EP (1) | EP1558613A2 (enExample) |
| JP (1) | JP2006514099A (enExample) |
| KR (1) | KR20050087787A (enExample) |
| CN (1) | CN100374438C (enExample) |
| AP (1) | AP1858A (enExample) |
| AU (2) | AU2003301439A1 (enExample) |
| BR (1) | BR0315405A (enExample) |
| CA (1) | CA2501881A1 (enExample) |
| EA (1) | EA011399B1 (enExample) |
| HR (1) | HRP20050431A2 (enExample) |
| IS (1) | IS7845A (enExample) |
| MX (1) | MXPA05003950A (enExample) |
| NO (1) | NO20052378L (enExample) |
| NZ (1) | NZ539264A (enExample) |
| OA (1) | OA13079A (enExample) |
| PL (1) | PL377966A1 (enExample) |
| UA (1) | UA79830C2 (enExample) |
| WO (2) | WO2004035577A2 (enExample) |
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| EP1183025B1 (en) * | 1999-05-19 | 2009-01-14 | PainCeptor Pharma Corp. | Inhibitors of proton-gated cation channels and their use in the treatment of ischaemic disorders |
| CA2522990A1 (en) * | 2003-04-28 | 2004-11-11 | Tibotec Pharmaceuticals Ltd. | Hiv integrase inhibitors |
| US20070185007A1 (en) * | 2003-09-19 | 2007-08-09 | Haolun Jin | Aza-quinolinol phosphonate integrase inhibitor compounds |
| AU2004297274B2 (en) * | 2003-12-08 | 2009-09-10 | The Research Foundation Of State University Of New York | Site selectively tagged and templated molecularly imprinted polymers for sensor applications |
| EP1694686A1 (en) | 2003-12-19 | 2006-08-30 | Takeda San Diego, Inc. | Kinase inhibitors |
| JP4682153B2 (ja) * | 2004-01-07 | 2011-05-11 | ザ リサーチ ファウンデイション オブ ステイト ユニバーシティー オブ ニューヨーク | 集積されたエミッションサイトを有するタンパク質インプリントポリマー |
| DE602005010413D1 (de) * | 2004-04-14 | 2008-11-27 | Zhenhong R Cai | Phosphonatanaloga von hiv-integrasehemmerverbindungen |
| US7538112B2 (en) * | 2004-05-07 | 2009-05-26 | Merck & Co., Inc. | HIV integrase inhibitors |
| US7476666B2 (en) | 2004-06-09 | 2009-01-13 | Merck & Co., Inc. | HIV integrase inhibitors |
| EP1778669A2 (en) | 2004-08-18 | 2007-05-02 | Takeda San Diego, Inc. | Kinase inhibitors |
| US7745459B2 (en) | 2004-09-21 | 2010-06-29 | Japan Tobacco Inc. | Quinolizinone compound and use thereof as HIV integrase inhibitor |
| ATE479687T1 (de) | 2004-10-15 | 2010-09-15 | Takeda Pharmaceutical | Kinaseinhibitoren |
| TW200716632A (en) * | 2005-05-16 | 2007-05-01 | Gilead Sciences Inc | Integrase inhibitor compounds |
| AU2006246930C1 (en) | 2005-05-19 | 2012-01-19 | Merck Canada Inc. | Quinoline derivatives as EP4 antagonists |
| AU2006272521A1 (en) * | 2005-07-27 | 2007-02-01 | Gilead Sciences, Inc. | Antiviral phosphonate conjugates for inhibition of HIV |
| WO2007019130A2 (en) * | 2005-08-04 | 2007-02-15 | Smithkline Beecham Corporation | Hiv integrase inhibitors |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP1973908A2 (en) * | 2005-12-21 | 2008-10-01 | Gilead Sciences, Inc. | Processes and intermediates useful for preparing integrase inhibitor compounds |
| EA018544B1 (ru) | 2005-12-30 | 2013-08-30 | Джилид Сайэнс, Инк. | Способ лечения ретровирусной инфекции |
| US20090233964A1 (en) * | 2005-12-30 | 2009-09-17 | Gilead Sciences, Inc. | Methods for improving the pharmacokinetics of hiv integrase inhibitors |
| NZ572367A (en) | 2006-05-16 | 2011-09-30 | Gilead Sciences Inc | Fused cyclic compounds as integrase inhibitors |
| JP2010505962A (ja) | 2006-10-09 | 2010-02-25 | 武田薬品工業株式会社 | キナーゼ阻害剤 |
| WO2009067541A2 (en) * | 2007-11-20 | 2009-05-28 | Gilead Sciences, Inc. | Integrase inhibitors |
| CN105055432A (zh) | 2008-01-25 | 2015-11-18 | 奇默里克斯公司 | 治疗病毒感染的方法 |
| SG192550A1 (en) | 2008-07-25 | 2013-08-30 | Viiv Healthcare Co | Chemical compounds |
| BRPI0916649A2 (pt) * | 2008-07-28 | 2015-08-04 | Polymedix Inc E The Trustees Of The University Of Pennsylvania | Composto, composição, uso de um composto, e, método para exterminar ou inibir o crescimento de uma espécie de plasmodium. |
| EP2376080B1 (en) | 2008-12-11 | 2017-09-13 | Shionogi&Co., Ltd. | Synthesis of carbamoylpyridone hiv integrase inhibitors and intermediates |
| EP2376453B1 (en) | 2008-12-11 | 2019-11-20 | VIIV Healthcare Company | Intermediates for carbamoylpyridone hiv integrase inhibitors |
| TWI518084B (zh) | 2009-03-26 | 2016-01-21 | 鹽野義製藥股份有限公司 | 哌喃酮與吡啶酮衍生物之製造方法 |
| EP2270021A1 (en) * | 2009-06-18 | 2011-01-05 | Centre National de la Recherche Scientifique | Phosphonates synthons for the synthesis of phosphonates derivatives showing better bioavailability |
| WO2011011483A1 (en) * | 2009-07-22 | 2011-01-27 | Glaxosmithkline Llc | Chemical compounds |
| ES2446720T3 (es) | 2009-10-13 | 2014-03-10 | Elanco Animal Health Ireland Limited | Inhibidores de la integrasa macrocíclica |
| US8283366B2 (en) | 2010-01-22 | 2012-10-09 | Ambrilia Biopharma, Inc. | Derivatives of pyridoxine for inhibiting HIV integrase |
| JP5745869B2 (ja) * | 2010-01-22 | 2015-07-08 | 富山化学工業株式会社 | アルアルキル基を有する複素環化合物 |
| ES2629165T3 (es) | 2010-02-12 | 2017-08-07 | Chimerix, Inc. | Métodos de tratamiento de una infección vírica |
| TWI582097B (zh) | 2010-03-23 | 2017-05-11 | Ｖｉｉｖ醫療保健公司 | 製備胺甲醯吡啶酮衍生物及中間體之方法 |
| TWI503323B (zh) * | 2010-03-29 | 2015-10-11 | Oncotherapy Science Inc | 三環化合物以及含此化合物之ｐｂｋ抑制劑 |
| RU2567385C2 (ru) | 2010-04-02 | 2015-11-10 | ЯНССЕН Ар ЭНД Ди АЙРЛЭНД | Макроциклические ингибиторы интегразы |
| ES2602794T3 (es) | 2011-03-31 | 2017-02-22 | Pfizer Inc | Piridinonas bicíclicas novedosas |
| US9089574B2 (en) | 2011-11-30 | 2015-07-28 | Emory University | Antiviral JAK inhibitors useful in treating or preventing retroviral and other viral infections |
| KR101365849B1 (ko) * | 2012-03-28 | 2014-02-24 | 경동제약 주식회사 | 솔리페나신 또는 그의 염의 제조방법 및 이에 사용되는 신규 중간체 |
| UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| US10260089B2 (en) | 2012-10-29 | 2019-04-16 | The Research Foundation Of The State University Of New York | Compositions and methods for recognition of RNA using triple helical peptide nucleic acids |
| LT3236972T (lt) | 2014-12-26 | 2021-11-10 | Emory University | Antivirusiniai n4-hidroksicitidino dariniai |
| MX368391B (es) | 2015-02-03 | 2019-09-30 | Pfizer | Ciclopropabenzofuranil-piridopirazindionas novedosas. |
| CN104803905B (zh) * | 2015-04-17 | 2017-10-10 | 复旦大学 | 一种合成异吲哚啉‑1‑酮衍生物的方法 |
| WO2017133517A1 (zh) * | 2016-02-03 | 2017-08-10 | 四川海思科制药有限公司 | 一种磷酰胺衍生物及制备方法和用途 |
| CN109305990B (zh) * | 2017-07-28 | 2021-02-26 | 四川海思科制药有限公司 | 一种磷酸衍生物及制备方法和用途 |
| CN109305989B (zh) * | 2017-07-28 | 2021-02-26 | 四川海思科制药有限公司 | 一种磷酰胺衍生物及制备方法和用途 |
| LT3706762T (lt) | 2017-12-07 | 2024-12-27 | Emory University | N4-hidroksicitidinas ir jo dariniai bei susiję naudojimo prieš virusus būdai |
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| CH385846A (de) * | 1960-03-31 | 1964-12-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen 7-Acyl-8-hydroxy-chinolinen und ihre Verwendung als Fungizide und Bakterizide im Pflanzen- und Materialschutz |
| US4816570A (en) * | 1982-11-30 | 1989-03-28 | The Board Of Regents Of The University Of Texas System | Biologically reversible phosphate and phosphonate protective groups |
| US4968788A (en) * | 1986-04-04 | 1990-11-06 | Board Of Regents, The University Of Texas System | Biologically reversible phosphate and phosphonate protective gruops |
| JP3347723B2 (ja) | 1990-06-13 | 2002-11-20 | グラツィエル，アーノルド | 含リンプロドラッグ |
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| DK0498722T3 (da) * | 1991-02-07 | 1998-03-09 | Roussel Uclaf | Nye bicycliske nitrogenforbindelser substitueret med en benzylgruppe, fremgangsmåde til deres fremstilling, de opnåede nye intermediærer, deres anvendelse som lægemidler og de pharmaceutiske præparater som de indgår i |
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| US6218402B1 (en) * | 1998-06-10 | 2001-04-17 | Arena Pharmaceuticals, Inc. | Acetylcholine enhancers |
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| WO2001027309A1 (en) * | 1999-10-13 | 2001-04-19 | Merck & Co., Inc. | Hiv integrase inhibitors |
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| JP2004517860A (ja) | 2000-10-12 | 2004-06-17 | メルク エンド カムパニー インコーポレーテッド | Ｈｉｖインテグラーゼ阻害薬として有用なアザ−およびポリアザ−ナフタレニルカルボキサミド類 |
| NZ525088A (en) * | 2000-10-12 | 2004-11-26 | Merck & Co Inc | Aza- and polyaza-naphthalenyl carboxamides useful as HIV integrase inhibitors |
| WO2002030970A2 (en) * | 2000-10-13 | 2002-04-18 | Bayer Aktiengesellschaft | Human histone deacetylase gene |
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| DE602005010413D1 (de) * | 2004-04-14 | 2008-11-27 | Zhenhong R Cai | Phosphonatanaloga von hiv-integrasehemmerverbindungen |
-
2003
- 2003-10-15 AU AU2003301439A patent/AU2003301439A1/en not_active Abandoned
- 2003-10-15 US US10/687,374 patent/US20040157804A1/en not_active Abandoned
- 2003-10-15 WO PCT/US2003/032866 patent/WO2004035577A2/en not_active Ceased
- 2003-10-16 EP EP03809030A patent/EP1558613A2/en not_active Withdrawn
- 2003-10-16 CA CA002501881A patent/CA2501881A1/en not_active Abandoned
- 2003-10-16 UA UAA200504480A patent/UA79830C2/uk unknown
- 2003-10-16 AU AU2003301306A patent/AU2003301306A1/en not_active Abandoned
- 2003-10-16 JP JP2005501423A patent/JP2006514099A/ja active Pending
- 2003-10-16 EA EA200500660A patent/EA011399B1/ru not_active IP Right Cessation
- 2003-10-16 OA OA1200500108A patent/OA13079A/en unknown
- 2003-10-16 HR HR20050431A patent/HRP20050431A2/hr not_active Application Discontinuation
- 2003-10-16 KR KR1020057006668A patent/KR20050087787A/ko not_active Ceased
- 2003-10-16 NZ NZ539264A patent/NZ539264A/en not_active IP Right Cessation
- 2003-10-16 PL PL377966A patent/PL377966A1/pl not_active Application Discontinuation
- 2003-10-16 CN CNB2003801061816A patent/CN100374438C/zh not_active Expired - Fee Related
- 2003-10-16 BR BR0315405-0A patent/BR0315405A/pt not_active IP Right Cessation
- 2003-10-16 WO PCT/US2003/032666 patent/WO2004035576A2/en not_active Ceased
- 2003-10-16 AP AP2005003279A patent/AP1858A/xx active
- 2003-10-16 MX MXPA05003950A patent/MXPA05003950A/es active IP Right Grant
- 2003-10-16 US US10/687,373 patent/US7253180B2/en not_active Expired - Fee Related
-
2005
- 2005-05-13 IS IS7845A patent/IS7845A/is unknown
- 2005-05-13 NO NO20052378A patent/NO20052378L/no not_active Application Discontinuation
-
2007
- 2007-05-25 US US11/807,303 patent/US20090029939A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AP1858A (en) | 2008-06-30 |
| NO20052378D0 (no) | 2005-05-13 |
| EA200500660A1 (ru) | 2005-10-27 |
| WO2004035577A2 (en) | 2004-04-29 |
| WO2004035576A3 (en) | 2004-06-24 |
| EP1558613A2 (en) | 2005-08-03 |
| AU2003301439A8 (en) | 2004-05-04 |
| OA13079A (en) | 2006-11-10 |
| US7253180B2 (en) | 2007-08-07 |
| AU2003301306A1 (en) | 2004-05-04 |
| NZ539264A (en) | 2007-08-31 |
| CN100374438C (zh) | 2008-03-12 |
| PL377966A1 (pl) | 2006-02-20 |
| US20040157804A1 (en) | 2004-08-12 |
| IS7845A (is) | 2005-05-13 |
| JP2006514099A (ja) | 2006-04-27 |
| BR0315405A (pt) | 2005-08-09 |
| AU2003301439A1 (en) | 2004-05-04 |
| WO2004035577A3 (en) | 2004-07-29 |
| NO20052378L (no) | 2005-07-18 |
| WO2004035576A2 (en) | 2004-04-29 |
| HRP20050431A2 (en) | 2005-10-31 |
| EA011399B1 (ru) | 2009-02-27 |
| US20040167124A1 (en) | 2004-08-26 |
| US20090029939A1 (en) | 2009-01-29 |
| CA2501881A1 (en) | 2004-04-29 |
| AP2005003279A0 (en) | 2005-06-30 |
| UA79830C2 (en) | 2007-07-25 |
| KR20050087787A (ko) | 2005-08-31 |
| CN1726212A (zh) | 2006-01-25 |
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