CA2479522A1 - New pharmaceutical compositions based on anticholinergics and p38 kinase inhibitors - Google Patents
New pharmaceutical compositions based on anticholinergics and p38 kinase inhibitors Download PDFInfo
- Publication number
- CA2479522A1 CA2479522A1 CA002479522A CA2479522A CA2479522A1 CA 2479522 A1 CA2479522 A1 CA 2479522A1 CA 002479522 A CA002479522 A CA 002479522A CA 2479522 A CA2479522 A CA 2479522A CA 2479522 A1 CA2479522 A1 CA 2479522A1
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- CA
- Canada
- Prior art keywords
- alkyl
- phenyl
- optionally
- amino
- optionally substituted
- 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.)
- Abandoned
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 96
- 229940043355 kinase inhibitor Drugs 0.000 title claims abstract description 84
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 title claims abstract description 84
- 239000003757 phosphotransferase inhibitor Substances 0.000 title claims abstract description 84
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 title claims abstract description 7
- 239000000812 cholinergic antagonist Substances 0.000 title claims abstract description 7
- -1 1,2,4-triazin-5-yl Chemical group 0.000 claims description 607
- 125000000217 alkyl group Chemical group 0.000 claims description 537
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 296
- 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 256
- 229910020008 S(O) Inorganic materials 0.000 claims description 183
- 229910052736 halogen Inorganic materials 0.000 claims description 182
- 150000002367 halogens Chemical class 0.000 claims description 182
- 125000000623 heterocyclic group Chemical group 0.000 claims description 182
- 125000003545 alkoxy group Chemical group 0.000 claims description 170
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 142
- 125000004076 pyridyl group Chemical group 0.000 claims description 136
- 125000001624 naphthyl group Chemical group 0.000 claims description 112
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 107
- 125000002883 imidazolyl group Chemical group 0.000 claims description 100
- 229910052760 oxygen Inorganic materials 0.000 claims description 100
- 125000003118 aryl group Chemical group 0.000 claims description 98
- 125000001072 heteroaryl group Chemical group 0.000 claims description 93
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 91
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 84
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 83
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 76
- 125000004043 oxo group Chemical group O=* 0.000 claims description 73
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 71
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 67
- 125000002541 furyl group Chemical group 0.000 claims description 67
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 67
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 67
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
- 125000001544 thienyl group Chemical group 0.000 claims description 61
- 229910052717 sulfur Inorganic materials 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 56
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 56
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 125000004193 piperazinyl group Chemical group 0.000 claims description 50
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 150000002825 nitriles Chemical class 0.000 claims description 45
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 44
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 43
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 43
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 43
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 41
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 38
- 125000003435 aroyl group Chemical group 0.000 claims description 38
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 34
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000013543 active substance Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 33
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 31
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 30
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 30
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 30
- 125000003282 alkyl amino group Chemical group 0.000 claims description 28
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 27
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 27
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 26
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 25
- 125000003386 piperidinyl group Chemical group 0.000 claims description 25
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 25
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 24
- 125000001041 indolyl group Chemical group 0.000 claims description 24
- 239000000843 powder Substances 0.000 claims description 24
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 23
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 22
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 22
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 20
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims description 20
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 20
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 20
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 20
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000443 aerosol Substances 0.000 claims description 18
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 18
- 239000003380 propellant Substances 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 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 17
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 17
- 229930192474 thiophene Natural products 0.000 claims description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 16
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 16
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 16
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- 238000009472 formulation Methods 0.000 claims description 15
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 15
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 14
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 12
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 12
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 12
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 12
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 12
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 12
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims description 11
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 11
- 239000002775 capsule Substances 0.000 claims description 11
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 11
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 11
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims description 11
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 10
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 10
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical class O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 claims description 9
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- 239000004615 ingredient Substances 0.000 claims description 8
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 150000003536 tetrazoles Chemical class 0.000 claims description 7
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 6
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 6
- 150000004677 hydrates Chemical class 0.000 claims description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 102220104380 rs199933920 Human genes 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 6
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- NVOYVOBDTVTBDX-PMEUIYRNSA-N oxitropium Chemical class CC[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1 NVOYVOBDTVTBDX-PMEUIYRNSA-N 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 5
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 claims description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 4
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37151402P | 2002-04-10 | 2002-04-10 | |
| US60/371,514 | 2002-04-10 | ||
| PCT/EP2003/003624 WO2003084539A2 (en) | 2002-04-10 | 2003-04-08 | New pharmaceutical compositions based on anticholinergics and p38 kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2479522A1 true CA2479522A1 (en) | 2003-10-16 |
Family
ID=28792055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002479522A Abandoned CA2479522A1 (en) | 2002-04-10 | 2003-04-08 | New pharmaceutical compositions based on anticholinergics and p38 kinase inhibitors |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20030225089A1 (https=) |
| EP (1) | EP1496900A2 (https=) |
| JP (1) | JP2005529098A (https=) |
| KR (1) | KR20050006149A (https=) |
| CN (1) | CN1658873A (https=) |
| AR (1) | AR039273A1 (https=) |
| AU (1) | AU2003224048A1 (https=) |
| BR (1) | BR0309099A (https=) |
| CA (1) | CA2479522A1 (https=) |
| MX (1) | MXPA04009772A (https=) |
| PE (1) | PE20040325A1 (https=) |
| PL (1) | PL372620A1 (https=) |
| RU (1) | RU2004133034A (https=) |
| TW (1) | TW200307681A (https=) |
| UY (1) | UY27755A1 (https=) |
| WO (1) | WO2003084539A2 (https=) |
| ZA (1) | ZA200407058B (https=) |
Families Citing this family (38)
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| GB0124939D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124933D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124934D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124941D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124936D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124931D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124938D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| ATE375980T1 (de) | 2002-02-12 | 2007-11-15 | Smithkline Beecham Corp | Nicotinamide und deren verwendung als p38 inhibitoren |
| ES2278170T3 (es) * | 2002-07-09 | 2007-08-01 | BOEHRINGER INGELHEIM PHARMA GMBH & CO.KG | Composiciones farmaceuticas de anticolinergicos e inhibidores de la quinasa p38 en el tratamiento de enfermedades respiratorias. |
| US20040044020A1 (en) * | 2002-07-09 | 2004-03-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmaceutical compositions based on novel anticholinergics and p38 kinase inhibitors |
| GB0217757D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
| US7144911B2 (en) * | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US7202257B2 (en) | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| GB0308185D0 (en) * | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| AU2004253967B2 (en) | 2003-07-03 | 2010-02-18 | Cytovia, Inc. | 4-arylamino-quinazolines as activators of caspases and inducers of apoptosis |
| WO2006074147A2 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics, Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| CA2536293A1 (en) * | 2003-08-22 | 2005-03-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Methods of treating copd and pulmonary hypertension |
| WO2005023761A2 (en) * | 2003-09-11 | 2005-03-17 | Kemia, Inc. | Cytokine inhibitors |
| GB0402143D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
| US20080051416A1 (en) * | 2004-10-05 | 2008-02-28 | Smithkline Beecham Corporation | Novel Compounds |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| GB0512429D0 (en) * | 2005-06-17 | 2005-07-27 | Smithkline Beecham Corp | Novel compound |
| US20070086957A1 (en) * | 2005-10-10 | 2007-04-19 | Thierry Bouyssou | Combination of medicaments for the treatment of respiratory diseases |
| EP1992344A1 (en) | 2007-05-18 | 2008-11-19 | Institut Curie | P38 alpha as a therapeutic target in pathologies linked to FGFR3 mutation |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| PL3089971T3 (pl) | 2014-01-01 | 2021-01-25 | Medivation Technologies Llc | Związki i sposoby ich zastosowania |
| US20190060286A1 (en) | 2016-02-29 | 2019-02-28 | University Of Florida Research Foundation, Incorpo | Chemotherapeutic Methods |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
| BR112020006677A2 (pt) | 2017-10-05 | 2020-10-06 | Fulcrum Therapeutics, Inc. | uso de inibidores p38 para reduzir a expressão de dux4 |
| CN118416236A (zh) | 2018-01-31 | 2024-08-02 | 德西费拉制药有限责任公司 | 治疗胃肠道间质瘤的组合疗法 |
| IL276398B2 (en) | 2018-01-31 | 2026-03-01 | Deciphera Pharmaceuticals Llc | Combination therapy for mastocytosis |
| WO2020185812A1 (en) | 2019-03-11 | 2020-09-17 | Teva Pharmaceuticals International Gmbh | Solid state forms of ripretinib |
| EP4013412B1 (en) | 2019-08-12 | 2026-01-28 | Deciphera Pharmaceuticals, LLC | Ripretinib for treating gastrointestinal stromal tumors |
| TWI878335B (zh) | 2019-08-12 | 2025-04-01 | 美商迪賽孚爾製藥有限公司 | 治療胃腸道基質瘤方法 |
| MX2022008103A (es) | 2019-12-30 | 2022-09-19 | Deciphera Pharmaceuticals Llc | Formulaciones de inhibidores de la cinasa amorfa y metodos de estas. |
| EP4084779B1 (en) | 2019-12-30 | 2024-10-09 | Deciphera Pharmaceuticals, LLC | Compositions of 1-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19536902A1 (de) * | 1995-10-04 | 1997-04-10 | Boehringer Ingelheim Int | Vorrichtung zur Hochdruckerzeugung in einem Fluid in Miniaturausführung |
| ZA97175B (en) * | 1996-01-11 | 1997-11-04 | Smithkline Beecham Corp | Novel substituted imidazole compounds. |
| EP0883402A4 (en) * | 1996-01-11 | 1999-08-11 | Smithkline Beecham Corp | NEW CYCLOALKYL-SUBSTITUTED IMIDAZOLES |
| AR016294A1 (es) * | 1997-07-02 | 2001-07-04 | Smithkline Beecham Corp | Compuesto de imidazol sustituido, composicion farmaceutica que la contiene, su uso en la fabricacion de un medicamento y procedimiento para supreparacion |
| KR100605140B1 (ko) * | 1998-05-22 | 2006-07-28 | 싸이오스 인크 | 심장병 및 다른 질병을 치료하기 위한 헤테로 고리 화합물및 그 치료 방법 |
| US6184226B1 (en) * | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
| MXPA01002173A (es) * | 1998-08-28 | 2003-07-14 | Scios Inc | Inhibidores de p38-alfa cinasa. |
| DE19847968A1 (de) * | 1998-10-17 | 2000-04-20 | Boehringer Ingelheim Pharma | Verschlußkappe und Behälter als Zweikammer-Kartusche für Vernebler zur Erzeugung von Aerosolen |
| US6492400B1 (en) * | 1998-12-18 | 2002-12-10 | Bristol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| ATE278674T1 (de) * | 1999-03-12 | 2004-10-15 | Boehringer Ingelheim Pharma | Heterocyklischer harnstoff und verwandte verbindungen als entzündungshemmende mittel |
| DE19921693A1 (de) * | 1999-05-12 | 2000-11-16 | Boehringer Ingelheim Pharma | Neuartige Arzneimittelkompositionen auf der Basis von anticholinergisch wirksamen Verbindungen und ß-Mimetika |
| DE60014681T2 (de) * | 1999-07-16 | 2006-02-02 | Leo Pharma A/S | Aminobenzophenone als inhibitoren von il-1beta und tnf-alpha |
| US6555710B1 (en) * | 1999-07-16 | 2003-04-29 | Leo Pharmaceutical Products Ltd A/S Lovens Kemiske Fabrik Produktionsaktieselskab | Aminobenzophenones as inhibitors of IL-1 β and TNF-α |
| AU768512B2 (en) * | 1999-07-16 | 2003-12-18 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Aminobenzophenones as inhibitors of IL-1beta and TNF-alpha |
| EP1210320B1 (en) * | 1999-07-16 | 2004-09-29 | Leo Pharma A/S | Aminobenzophenones as inhibitors of il-1beta and tnf-alpha |
| KR20020013961A (ko) * | 1999-07-16 | 2002-02-21 | 룬딩 에른스트 | 신규한 아미노벤조페논 |
| US6387900B1 (en) * | 1999-08-12 | 2002-05-14 | Pharmacia & Upjohn S.P.A. | 3(5)-ureido-pyrazole derivatives process for their preparation and their use as antitumor agents |
| US6608052B2 (en) * | 2000-02-16 | 2003-08-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
| WO2002083642A1 (en) * | 2001-04-13 | 2002-10-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
| JP2004530690A (ja) * | 2001-05-16 | 2004-10-07 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 抗炎症性薬剤として有用なジアリールウレア誘導体 |
| GB0129273D0 (en) * | 2001-12-06 | 2002-01-23 | Pfizer Ltd | Crystalline drug form |
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2003
- 2003-04-07 US US10/408,718 patent/US20030225089A1/en not_active Abandoned
- 2003-04-08 TW TW092107993A patent/TW200307681A/zh unknown
- 2003-04-08 JP JP2003581779A patent/JP2005529098A/ja active Pending
- 2003-04-08 KR KR10-2004-7016160A patent/KR20050006149A/ko not_active Withdrawn
- 2003-04-08 AU AU2003224048A patent/AU2003224048A1/en not_active Abandoned
- 2003-04-08 BR BR0309099-0A patent/BR0309099A/pt not_active IP Right Cessation
- 2003-04-08 CN CN038134217A patent/CN1658873A/zh active Pending
- 2003-04-08 CA CA002479522A patent/CA2479522A1/en not_active Abandoned
- 2003-04-08 RU RU2004133034/15A patent/RU2004133034A/ru not_active Application Discontinuation
- 2003-04-08 EP EP03720433A patent/EP1496900A2/en not_active Withdrawn
- 2003-04-08 PL PL03372620A patent/PL372620A1/xx not_active Application Discontinuation
- 2003-04-08 MX MXPA04009772A patent/MXPA04009772A/es unknown
- 2003-04-08 WO PCT/EP2003/003624 patent/WO2003084539A2/en not_active Ceased
- 2003-04-08 PE PE2003000353A patent/PE20040325A1/es not_active Application Discontinuation
- 2003-04-09 AR ARP030101239A patent/AR039273A1/es unknown
- 2003-04-09 UY UY27755A patent/UY27755A1/es not_active Application Discontinuation
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2004
- 2004-09-03 ZA ZA200407058A patent/ZA200407058B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| UY27755A1 (es) | 2003-11-28 |
| WO2003084539A3 (en) | 2004-09-02 |
| AR039273A1 (es) | 2005-02-16 |
| PL372620A1 (en) | 2005-07-25 |
| KR20050006149A (ko) | 2005-01-15 |
| CN1658873A (zh) | 2005-08-24 |
| PE20040325A1 (es) | 2004-07-08 |
| JP2005529098A (ja) | 2005-09-29 |
| RU2004133034A (ru) | 2006-06-20 |
| TW200307681A (en) | 2003-12-16 |
| MXPA04009772A (es) | 2004-12-13 |
| AU2003224048A1 (en) | 2003-10-20 |
| BR0309099A (pt) | 2005-03-29 |
| EP1496900A2 (en) | 2005-01-19 |
| ZA200407058B (en) | 2006-06-28 |
| WO2003084539A2 (en) | 2003-10-16 |
| US20030225089A1 (en) | 2003-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |