ES2275567T3 - Mimeticos de4 trombopoietina. - Google Patents
Mimeticos de4 trombopoietina. Download PDFInfo
- Publication number
- ES2275567T3 ES2275567T3 ES00984123T ES00984123T ES2275567T3 ES 2275567 T3 ES2275567 T3 ES 2275567T3 ES 00984123 T ES00984123 T ES 00984123T ES 00984123 T ES00984123 T ES 00984123T ES 2275567 T3 ES2275567 T3 ES 2275567T3
- Authority
- ES
- Spain
- Prior art keywords
- hydroxy
- imidazol
- acid
- sulfonic
- naphth
- 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.)
- Expired - Lifetime
Links
- 102000036693 Thrombopoietin Human genes 0.000 title description 42
- 108010041111 Thrombopoietin Proteins 0.000 title description 42
- 206010043554 thrombocytopenia Diseases 0.000 claims abstract description 17
- 241000124008 Mammalia Species 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims description 644
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 339
- 150000001875 compounds Chemical class 0.000 claims description 263
- -1 4-hydroxy-cyclohexyl Chemical group 0.000 claims description 253
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
- RIXQDZPQQARWPF-UHFFFAOYSA-N 2-[3-(3,4-dimethylphenyl)-4-fluorophenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=CC=C1F RIXQDZPQQARWPF-UHFFFAOYSA-N 0.000 claims description 7
- DHDPRFWMBZYBHQ-UHFFFAOYSA-N 2-[3-(4-tert-butylphenyl)-4-fluorophenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=CC=C1F DHDPRFWMBZYBHQ-UHFFFAOYSA-N 0.000 claims description 7
- YUYKKHRGDBTSCO-UHFFFAOYSA-N 2-[4-(4-tert-butylphenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=COC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 YUYKKHRGDBTSCO-UHFFFAOYSA-N 0.000 claims description 7
- JRQVQXMCEHOMTD-UHFFFAOYSA-N 2-[4-(4-tert-butylphenyl)thiophen-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CSC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 JRQVQXMCEHOMTD-UHFFFAOYSA-N 0.000 claims description 7
- AFIXYXZIEDFJSQ-UHFFFAOYSA-N 2-[5-(4-tert-butylphenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)O1 AFIXYXZIEDFJSQ-UHFFFAOYSA-N 0.000 claims description 7
- IYUUWMOKXYWEKS-UHFFFAOYSA-N 2-[5-(4-tert-butylphenyl)thiophen-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)S1 IYUUWMOKXYWEKS-UHFFFAOYSA-N 0.000 claims description 7
- FZUAAPXAGQKWTR-UHFFFAOYSA-N 9-hydroxy-2-[3-[4-(trifluoromethyl)phenyl]phenyl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 FZUAAPXAGQKWTR-UHFFFAOYSA-N 0.000 claims description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
- 150000004677 hydrates Chemical class 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- JUTHBNVXQXOKAW-UHFFFAOYSA-N 2-[4-(3,4-dimethylphenyl)thiophen-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CSC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 JUTHBNVXQXOKAW-UHFFFAOYSA-N 0.000 claims description 6
- JGVUAKWZVVQDIZ-UHFFFAOYSA-N 2-[5-(1-benzothiophen-2-yl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC=C2SC(C3=CC=C(O3)C3=NC=4C5=C(O)C=C(C=C5C=CC=4N3)C(=O)O)=CC2=C1 JGVUAKWZVVQDIZ-UHFFFAOYSA-N 0.000 claims description 6
- BVFJXHBESHGUAG-UHFFFAOYSA-N 2-[5-(3,4-dichlorophenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(O1)=CC=C1C1=CC=C(Cl)C(Cl)=C1 BVFJXHBESHGUAG-UHFFFAOYSA-N 0.000 claims description 6
- MRINVXQHKAFPJM-UHFFFAOYSA-N 2-[5-(3,4-dimethylphenyl)-2-fluorophenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=C(F)C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 MRINVXQHKAFPJM-UHFFFAOYSA-N 0.000 claims description 6
- BZFLTSNUYALYDP-UHFFFAOYSA-N 2-[5-(4-tert-butylphenyl)-2-fluorophenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(F)C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 BZFLTSNUYALYDP-UHFFFAOYSA-N 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- CCDYVLRMODKYBN-UHFFFAOYSA-N 2-[3-(3,4-difluorophenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(C=1)=CC=CC=1C1=CC=C(F)C(F)=C1 CCDYVLRMODKYBN-UHFFFAOYSA-N 0.000 claims description 5
- FMMBNUOLITXBJH-UHFFFAOYSA-N 2-[3-(4-ethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(CC)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 FMMBNUOLITXBJH-UHFFFAOYSA-N 0.000 claims description 5
- WDPVPCHFYXVZBH-UHFFFAOYSA-N 2-[3-(4-fluoro-3-methylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(F)C(C)=CC(C=2C=C(C=CC=2)C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 WDPVPCHFYXVZBH-UHFFFAOYSA-N 0.000 claims description 5
- UUCZHGTVNCOOGT-UHFFFAOYSA-N 2-[3-(4-tert-butylphenyl)-4-methoxyphenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound COC1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)C=C1C1=CC=C(C(C)(C)C)C=C1 UUCZHGTVNCOOGT-UHFFFAOYSA-N 0.000 claims description 5
- URPRRKYQUKYLLB-UHFFFAOYSA-N 2-[5-(3,4-dimethylphenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)O1 URPRRKYQUKYLLB-UHFFFAOYSA-N 0.000 claims description 5
- NBZHPHMNNFTTGT-UHFFFAOYSA-N 2-[5-(3,4-dimethylphenyl)thiophen-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)S1 NBZHPHMNNFTTGT-UHFFFAOYSA-N 0.000 claims description 5
- UDKWCHCYYXBFLF-UHFFFAOYSA-N 9-hydroxy-2-[3-(4-propylphenyl)phenyl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(CCC)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 UDKWCHCYYXBFLF-UHFFFAOYSA-N 0.000 claims description 5
- VHVGKHMMCSHNKO-UHFFFAOYSA-N 9-hydroxy-2-[5-[4-(trifluoromethyl)phenyl]furan-2-yl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(O1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VHVGKHMMCSHNKO-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- IDFUAIXQXIJJAT-VWLOTQADSA-N (2s)-1-[[2-[3-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazol-7-yl]sulfonyl]pyrrolidine-2-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(=O)(=O)N3[C@@H](CCC3)C(O)=O)N=2)=C1 IDFUAIXQXIJJAT-VWLOTQADSA-N 0.000 claims description 4
- HMYQKSCWAIVMPA-UHFFFAOYSA-N 2-[1-(4-tert-butylphenyl)pyrazol-4-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1N1N=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 HMYQKSCWAIVMPA-UHFFFAOYSA-N 0.000 claims description 4
- ZSVLXFZCIUIOQN-UHFFFAOYSA-N 2-[3-(4-butylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(CCCC)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 ZSVLXFZCIUIOQN-UHFFFAOYSA-N 0.000 claims description 4
- MJOUJSVVDLUTNU-UHFFFAOYSA-N 2-[3-(4-cyano-3-methylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C#N)C(C)=CC(C=2C=C(C=CC=2)C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 MJOUJSVVDLUTNU-UHFFFAOYSA-N 0.000 claims description 4
- NLMFQHLOROEZBE-UHFFFAOYSA-N 2-[3-(9h-fluoren-2-yl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC(C2=NC=3C4=C(O)C=C(C=C4C=CC=3N2)C(=O)O)=CC=C1 NLMFQHLOROEZBE-UHFFFAOYSA-N 0.000 claims description 4
- OTZGPXBQZJFLQX-UHFFFAOYSA-N 2-[4-(3,4-dimethylphenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=COC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 OTZGPXBQZJFLQX-UHFFFAOYSA-N 0.000 claims description 4
- YDDZHDBISXIDKD-UHFFFAOYSA-N 3-[[2-[3-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazol-7-yl]sulfonylamino]benzoic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(=O)(=O)NC=3C=C(C=CC=3)C(O)=O)N=2)=C1 YDDZHDBISXIDKD-UHFFFAOYSA-N 0.000 claims description 4
- PRRDCKYEDGCCLO-UHFFFAOYSA-N 9-hydroxy-2-[5-(3-propan-2-ylphenyl)furan-2-yl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound CC(C)C1=CC=CC(C=2OC(=CC=2)C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 PRRDCKYEDGCCLO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- WJRLZGRPVWMNFM-UHFFFAOYSA-N 1,4-difluoro-2-phenyl-5-(trifluoromethyl)benzene Chemical group FC1=CC(=C(F)C=C1C(F)(F)F)C1=CC=CC=C1 WJRLZGRPVWMNFM-UHFFFAOYSA-N 0.000 claims description 3
- VBYPCJIAVPFBDO-UHFFFAOYSA-N 1-fluoro-4-[4-(trifluoromethyl)phenyl]benzene Chemical group C1=CC(F)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VBYPCJIAVPFBDO-UHFFFAOYSA-N 0.000 claims description 3
- YIGCYXIJBYEWHG-UHFFFAOYSA-N 2-[3-(4-carboxy-3-methylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2C=C(C=CC=2)C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 YIGCYXIJBYEWHG-UHFFFAOYSA-N 0.000 claims description 3
- CEWMMRRJLMXMNM-UHFFFAOYSA-N 2-[3-(4-tert-butylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 CEWMMRRJLMXMNM-UHFFFAOYSA-N 0.000 claims description 3
- AGWRYRHIQJXNLW-UHFFFAOYSA-N 2-[5-(4-tert-butylphenyl)pyridin-3-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CN=CC(C=2NC3=C4C(O)=CC(=CC4=CC=C3N=2)C(O)=O)=C1 AGWRYRHIQJXNLW-UHFFFAOYSA-N 0.000 claims description 3
- UFTVNMRVQIUXPU-UHFFFAOYSA-N 2-[6-(4-tert-butylphenyl)pyridin-2-yl]-9-hydroxy-3H-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=N1 UFTVNMRVQIUXPU-UHFFFAOYSA-N 0.000 claims description 3
- ITRBTOXCUXWGGG-UHFFFAOYSA-N 2-fluoro-1-phenyl-4-(trifluoromethyl)benzene Chemical group FC1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1 ITRBTOXCUXWGGG-UHFFFAOYSA-N 0.000 claims description 3
- DXSQQJMOMUMDRZ-UHFFFAOYSA-N 9-hydroxy-2-(3-phenoxyphenyl)-3h-benzo[e]benzimidazole-7-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(C=1)=CC=CC=1OC1=CC=CC=C1 DXSQQJMOMUMDRZ-UHFFFAOYSA-N 0.000 claims description 3
- OFGYBOHAQNSGKW-UHFFFAOYSA-N 9-hydroxy-2-[4-[4-(trifluoromethyl)phenyl]thiophen-2-yl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(SC=1)=CC=1C1=CC=C(C(F)(F)F)C=C1 OFGYBOHAQNSGKW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- KUOCSFZNWSSKNQ-UHFFFAOYSA-N 2-[4-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)C=C1 KUOCSFZNWSSKNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims description 2
- AOWUASXGYDUMKM-UHFFFAOYSA-N 9-hydroxy-2-(1-hydroxynaphthalen-2-yl)-3H-benzo[e]benzimidazole-7-carboxylic acid 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.OC1=C(C=CC2=CC=CC=C12)C=1NC2=C(N1)C1=C(C=C(C=C1C=C2)C(=O)O)O AOWUASXGYDUMKM-UHFFFAOYSA-N 0.000 claims description 2
- VYZIIAYKVGFVLA-UHFFFAOYSA-N 9-hydroxy-2-(4-phenylphenyl)-3h-benzo[e]benzimidazole-7-sulfonic acid;hydrochloride Chemical compound Cl.N=1C2=C3C(O)=CC(S(O)(=O)=O)=CC3=CC=C2NC=1C(C=C1)=CC=C1C1=CC=CC=C1 VYZIIAYKVGFVLA-UHFFFAOYSA-N 0.000 claims description 2
- SCEWJWDMGYCDCP-UHFFFAOYSA-N 9-hydroxy-2-pyridin-2-yl-3H-benzo[e]benzimidazole-7-carboxylic acid 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.N1=C(C=CC=C1)C=1NC2=C(N1)C1=C(C=C(C=C1C=C2)C(=O)O)O SCEWJWDMGYCDCP-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
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- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000003343 megakaryocytopoietic effect Effects 0.000 description 1
- ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical compound COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940045847 receptor mimetic Drugs 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KSVSZLXDULFGDQ-UHFFFAOYSA-M sodium;4-aminobenzenesulfonate Chemical compound [Na+].NC1=CC=C(S([O-])(=O)=O)C=C1 KSVSZLXDULFGDQ-UHFFFAOYSA-M 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000035921 thrombopoiesis Effects 0.000 description 1
- 230000001361 thrombopoietic effect Effects 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16913099P | 1999-12-06 | 1999-12-06 | |
| US169130P | 1999-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2275567T3 true ES2275567T3 (es) | 2007-06-16 |
Family
ID=22614367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00984123T Expired - Lifetime ES2275567T3 (es) | 1999-12-06 | 2000-12-06 | Mimeticos de4 trombopoietina. |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1244446B1 (enExample) |
| JP (1) | JP2003515560A (enExample) |
| AT (1) | ATE344031T1 (enExample) |
| AU (1) | AU2079901A (enExample) |
| DE (1) | DE60031714T2 (enExample) |
| ES (1) | ES2275567T3 (enExample) |
| WO (1) | WO2001039773A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7851503B2 (en) | 2002-08-14 | 2010-12-14 | Nissan Chemical Industries, Ltd. | Thrombopoetin receptor activator and process for producing the same |
| TWI324593B (en) | 2002-10-09 | 2010-05-11 | Nissan Chemical Ind Ltd | Pyrazolone compounds and thrombopoietin receptor activator |
| PT1569912E (pt) | 2002-12-03 | 2015-09-15 | Pharmacyclics Llc | Derivados 2-(2-hidroxibifenil-3-il)-1h-benzoimidazole-5- carboxamidina como inibidores do fator viia |
| US8030336B2 (en) * | 2002-12-13 | 2011-10-04 | Ym Biosciences Australia Pty Ltd | Nicotinamide-based kinase inhibitors |
| EP1581527A4 (en) * | 2002-12-13 | 2006-11-22 | Smithkline Beecham Corp | MIMETICS OF THROMBOPOIETINE |
| TW200418791A (en) * | 2003-01-23 | 2004-10-01 | Bristol Myers Squibb Co | Pharmaceutical compositions for inhibiting proteasome |
| CN101031539A (zh) | 2003-08-14 | 2007-09-05 | 旭化成制药株式会社 | 取代的芳基链烷酸衍生物及其用途 |
| US8729117B2 (en) | 2004-06-02 | 2014-05-20 | Pharmacyclics, Inc. | Factor VIIa inhibitor |
| US8552031B2 (en) | 2004-12-08 | 2013-10-08 | Nissan Chemical Industries, Ltd. | 3-ethylidenehydrazino substituted heterocyclic compounds as thrombopoietin receptor activators |
| AU2005314788B2 (en) | 2004-12-14 | 2011-09-22 | Nissan Chemical Industries, Ltd. | Amide compound and thrombopoietin receptor activator |
| PT1910338E (pt) * | 2005-07-14 | 2010-12-02 | Irm Llc | Compostos heterotetracíclicos como miméticos de tpo |
| EP1904472A1 (en) | 2005-07-15 | 2008-04-02 | Nissan Chemical Industries, Ltd. | Thiophene compounds and thrombopoietin receptor activators |
| KR101290484B1 (ko) | 2005-07-20 | 2013-07-26 | 닛산 가가쿠 고교 가부시키 가이샤 | 피라졸 화합물 및 트롬보포이에틴 수용체 활성화제 |
| CN101282929A (zh) * | 2005-08-15 | 2008-10-08 | Irm责任有限公司 | 用作tpo模拟物的化合物和组合物 |
| EP1947101A4 (en) | 2005-11-07 | 2009-09-16 | Nissan Chemical Ind Ltd | HYDRAZIDE COMPOUND AND THROMBOPOIETIN RECEPTOR ACTIVATOR |
| US8093251B2 (en) | 2006-06-07 | 2012-01-10 | Nissan Chemical Industries, Ltd. | Nitrogen-containing heterocyclic compounds and thrombopoietin receptor activators |
| ES2438240T3 (es) | 2006-07-11 | 2014-01-16 | Daewoong Pharmaceutical Co., Ltd. | Nuevos derivados de biaril benzoimidazol y composición farmacéutica que los comprenden |
| ES2392117T3 (es) | 2007-04-30 | 2012-12-04 | Abbott Laboratories | Inhibidores de enzima diacilglicerol O-aciltransferasa de tipo 1 |
| CN101481352A (zh) | 2008-01-10 | 2009-07-15 | 上海恒瑞医药有限公司 | 双环取代吡唑酮偶氮类衍生物、其制备方法及其在医药上的应用 |
| PE20100362A1 (es) | 2008-10-30 | 2010-05-27 | Irm Llc | Derivados de purina que expanden las celulas madre hematopoyeticas |
| CN101921232A (zh) | 2009-06-11 | 2010-12-22 | 上海恒瑞医药有限公司 | 双环取代吡唑酮偶氮类衍生物的盐,其制备方法及其在医药上的应用 |
| WO2012102937A2 (en) | 2011-01-25 | 2012-08-02 | Irm Llc | Compounds that expand hematopoietic stem cells |
| HK1203081A1 (en) | 2011-12-08 | 2015-10-16 | Fred Hutchinson Cancer Research Center | Compositions and methods for enhanced generation of hematopoietic stem/progenitor cells |
| JP6250556B2 (ja) | 2012-01-27 | 2017-12-20 | ユニヴェルスィテ・ドゥ・モントリオール | ピリミド［４，５−ｂ］インドール誘導体及び造血幹細胞の増殖におけるその使用 |
| ES2788977T3 (es) | 2014-04-22 | 2020-10-23 | Univ Montreal | Compuestos y uso de los mismos en la expansión de células madre hematopoyéticas y/o células progenitoras hematopoyéticas |
| TW201615228A (zh) | 2014-10-31 | 2016-05-01 | Nissan Chemical Ind Ltd | 配體結合纖維及使用該纖維之細胞培養基材 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE193350C (enExample) * | ||||
| US851444A (en) * | 1905-11-13 | 1907-04-23 | Agfa Ag | Amido-oxy-sulfonic acid of phenylnaphthimidazol and process of making same. |
| US4435417A (en) * | 1981-02-20 | 1984-03-06 | Gruppo Lepetit S.P.A. | Antiinflammatory 3H-naphtho[1,2-d]imidazoles |
| DE4126612A1 (de) * | 1990-08-14 | 1992-02-20 | Ciba Geigy Ag | Reaktivfarbstoffe, deren herstellung und verwendung |
| PT98673B (pt) * | 1990-08-15 | 1999-01-29 | British Bio Technology | Processo para a preparacao de compostos que sao antagonistas do factor de activacao de plaquetas por exemplo derivados de benzimidazole e de seus intermediarios |
-
2000
- 2000-12-06 ES ES00984123T patent/ES2275567T3/es not_active Expired - Lifetime
- 2000-12-06 AU AU20799/01A patent/AU2079901A/en not_active Abandoned
- 2000-12-06 JP JP2001541505A patent/JP2003515560A/ja active Pending
- 2000-12-06 WO PCT/US2000/033432 patent/WO2001039773A1/en not_active Ceased
- 2000-12-06 DE DE60031714T patent/DE60031714T2/de not_active Expired - Fee Related
- 2000-12-06 AT AT00984123T patent/ATE344031T1/de not_active IP Right Cessation
- 2000-12-06 EP EP00984123A patent/EP1244446B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1244446A4 (en) | 2003-01-08 |
| DE60031714T2 (de) | 2007-09-06 |
| DE60031714D1 (de) | 2006-12-14 |
| WO2001039773A1 (en) | 2001-06-07 |
| EP1244446A1 (en) | 2002-10-02 |
| AU2079901A (en) | 2001-06-12 |
| JP2003515560A (ja) | 2003-05-07 |
| ATE344031T1 (de) | 2006-11-15 |
| EP1244446B1 (en) | 2006-11-02 |
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