JP2009515887A5 - - Google Patents

Info

Publication number

JP2009515887A5

JP2009515887A5 JP2008540207A JP2008540207A JP2009515887A5 JP 2009515887 A5 JP2009515887 A5 JP 2009515887A5 JP 2008540207 A JP2008540207 A JP 2008540207A JP 2008540207 A JP2008540207 A JP 2008540207A JP 2009515887 A5 JP2009515887 A5 JP 2009515887A5

Authority

JP

Japan

Prior art keywords

aminophenyl

methoxyphenyl

methylphenyl

formula

compound

Prior art date

2006-11-10

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

• Espacenet
• Global Dossier
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• -1 4-methoxyphenyl 2,4-dimethoxyphenyl Chemical group 0.000 claims 89
• 150000001875 compounds Chemical class 0.000 claims 32
• 239000000203 mixture Substances 0.000 claims 17
• ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 14
• 208000024412 Friedreich ataxia Diseases 0.000 claims 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 12
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 12
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 12
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 12
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 12
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 12
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 12
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 12
• 241000124008 Mammalia Species 0.000 claims 11
• 238000000034 method Methods 0.000 claims 11
• 150000003839 salts Chemical class 0.000 claims 9
• 108020004999 messenger RNA Proteins 0.000 claims 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 4
• 150000007514 bases Chemical class 0.000 claims 4
• 239000008194 pharmaceutical composition Substances 0.000 claims 4
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
• 108090000217 Frataxin Proteins 0.000 claims 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
• 239000002585 base Substances 0.000 claims 3
• 239000012024 dehydrating agents‎ Substances 0.000 claims 3
• 239000003814 drug Substances 0.000 claims 3
• 238000004519 manufacturing process Methods 0.000 claims 3
• 239000002904 solvent Substances 0.000 claims 3
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
• 102000003869 Frataxin Human genes 0.000 claims 2
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
• 239000007822 coupling agent Substances 0.000 claims 2
• 230000006195 histone acetylation Effects 0.000 claims 2
• BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 claims 2
• 239000003960 organic solvent Substances 0.000 claims 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
• 206010003591 Ataxia Diseases 0.000 claims 1
• 102000003964 Histone deacetylase Human genes 0.000 claims 1
• 108090000353 Histone deacetylase Proteins 0.000 claims 1
• 239000002253 acid Substances 0.000 claims 1
• 229910052783 alkali metal Inorganic materials 0.000 claims 1
• 150000001340 alkali metals Chemical class 0.000 claims 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
• 150000001342 alkaline earth metals Chemical class 0.000 claims 1
• 150000003973 alkyl amines Chemical class 0.000 claims 1
• 150000001412 amines Chemical class 0.000 claims 1
• 229910021529 ammonia Inorganic materials 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 claims 1
• 239000002775 capsule Substances 0.000 claims 1
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
• 238000004587 chromatography analysis Methods 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 238000001914 filtration Methods 0.000 claims 1
• 238000009472 formulation Methods 0.000 claims 1
• 229940121372 histone deacetylase inhibitor Drugs 0.000 claims 1
• 239000003276 histone deacetylase inhibitor Substances 0.000 claims 1
• 230000002401 inhibitory effect Effects 0.000 claims 1
• 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
• 238000001990 intravenous administration Methods 0.000 claims 1
• 239000011707 mineral Substances 0.000 claims 1
• 150000007524 organic acids Chemical class 0.000 claims 1
• 238000007911 parenteral administration Methods 0.000 claims 1
• 238000001556 precipitation Methods 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 238000001953 recrystallisation Methods 0.000 claims 1
• 238000013268 sustained release Methods 0.000 claims 1
• 239000012730 sustained-release form Substances 0.000 claims 1
• 230000002194 synthesizing effect Effects 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
• 0 C*(C)C(N(O*)I)=O Chemical compound C*(C)C(N(O*)I)=O 0.000 description 3