RU2004122915A - Ингибиторы продуцирования / секреции b-амилоидного белка - Google Patents

Ингибиторы продуцирования / секреции b-амилоидного белка Download PDF

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RU2004122915A
RU2004122915A RU2004122915/04A RU2004122915A RU2004122915A RU 2004122915 A RU2004122915 A RU 2004122915A RU 2004122915/04 A RU2004122915/04 A RU 2004122915/04A RU 2004122915 A RU2004122915 A RU 2004122915A RU 2004122915 A RU2004122915 A RU 2004122915A
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alkyl
groups
amino
alkylamino
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RU2004122915/04A
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RU2304140C2 (ru
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Таканори ЯСУКОУТИ (JP)
Таканори ЯСУКОУТИ
Масаюки ИТО (JP)
Масаюки ИТО
Хидеки КУБОТА (JP)
Хидеки КУБОТА
Сатору МИЯУТИ (JP)
Сатору МИЯУТИ
Масанори САИТО (JP)
Масанори САИТО
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Дайити Фармасьютикал Ко., Лтд. (JP)
Дайити Фармасьютикал Ко., Лтд.
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
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    • C07D211/24—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by sulfur atoms to which a second hetero atom is attached
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Claims (16)

Измененная формула изобретения, предложенная заявителем для рассмотрения
1. Соединение, представленное следующей формулой (3):
Figure 00000001
(где R15 представляет гетероциклическую группу, которая может иметь заместитель, R16 представляет циклическую углеводородную группу, которая может иметь заместитель, или гетероциклическую группу, которая может иметь заместитель, R17 представляет циклическую углеводородную группу, которая может иметь заместитель, или гетероциклическую группу, которая может иметь заместитель, R18 представляет атом водорода или С1-6алкильную группу, а Х представляет –S-, -SO- или –SO2-); или N-оксид или S-оксид данного соединения; их соль; или сольват описанного выше соединения.
2. Соединение по п.1, где Х представляет –SO- или –SO2-; или N-оксид или S-оксид данного соединения; их соль; или сольват описанного выше соединения.
3. Соединение по п.1, где Х представляет –SO2-; или N-оксид или S-оксид данного соединения; их соль; или сольват описанного выше соединения.
4. Соединение по любому из пп.1-3, где гетероциклическая группа, представленная R15, R16 или R17, является 3-7-членной насыщенной или 4-7-членной ненасыщенной моноциклической гетероциклической группой, имеющей 1-4 атома, выбранных из атома азота, атома кислорода и атома серы, или 7-14-членной полициклической гетероциклической группой, имеющей 1-4 атома, выбранных из атома азота, атома кислорода и атома серы; или N-оксид или S-оксид данного соединения; их соль; или сольват описанного выше соединения.
5. Соединение по любому из пп.1-3, где циклическая углеводородная группа, представленная R16 или R17, является циклоалкильной группой имеющей 3-7 атомов углерода, циклоалкенильной группой, имеющей 4-7 атомов углерода, моноциклической или полициклической ароматической углеводородной группой, имеющей 6-14 атомов углерода, спироуглеводородной группой, имеющей 7-11 атомов углерода, циклической углеводородной группой с поперечными (мостиковыми) связями, имеющей 7-10 атомов углерода, или конденсированной углеводородной группой, имеющей 8-14 атомов углерода; или N-оксид или S-оксид данного соединения; их соль; или сольват описанного выше соединения.
6. Соединение по любому из пп.1-3, где заместителем для циклической углеводородной группы или гетероциклической группы, представленной R15, R16 или R17, является группа –Q201-Q202-Q203-Q204–Q205-Q206-Q207, где Q201 представляет простую связь, алкильную группу, имеющую 1-6 атомов углерода, алкенильную группу, имеющую 2-6 атомов углерода или гетероциклическую группу; Q202 представляет простую связь, -О-, -NH-, -CH=N-, -С(алкил)=N-, -N(алкил)- или –S-; Q203 представляет простую связь, -СО-, -CS-, -SO-, -SO2- или –CONH-; Q204 представляет простую связь, алкильную группу, имеющую 1-6 атомов углерода, алкенильную группу, имеющую 2-6 атомов углерода, циклоалкильную группу, циклоалкенильную группу, ароматическую углеводородную группу или гетероциклическую группу; Q205 представляет простую связь, -NH- или –N(алкил)-; Q206 представляет простую связь, -О-, -СО-, -CS-, -SO2-, -SO- или –S-; и Q207 представляет атом водорода, атом галогена, гидроксигруппу, оксогруппу,
С1-6алкильную группу, С2-6алкенильную группу,
С3-8циклоалкильную группу, С1-6алкоксигруппу,
С2-6алкенилоксигруппу, азидогруппу, цианогруппу, аминогруппу,
С1-6алкиламиногруппу, ди(С1-6алкил)аминогруппу,
С2-6алканоиламиногруппу, ди(С2-6алканоил)аминогруппу,
карбоксиаминогруппу, С1-6алкоксикарбониламиногруппу,
ди(С1-6алкокси)карбониламиногруппу, гетероциклическую группу,
ароматическую углеводородную группу, циклоалкенильную группу,
гетероциклилоксигруппу или ароматический углеводородоксигруппу,
(где алкильная группа, имеющая 1-6 атомов углерода, алкенильная группа, имеющая 2-6 атомов углерода, циклоалкильная группа, циклоалкенильная группа, гетероциклическая группа, гетероциклическая оксигруппа, ароматическая углеводородная группа или ароматический углеводородоксигруппа может быть замещена 1-3 заместителями, выбранными из атомов галогена,
С1-6алкильных групп, С1-6алкоксигрупп, С2-6алкенильных групп,
карбоксиамино-С1-6алкильных групп,
С1-6алкоксикарбониламино-С1-6алкильных групп,
формильной группы, С2-6алканоильных групп, оксогруппы,
нитрогруппы, цианогруппы, азидогруппы, амидиногруппы,
С2-6алкенилоксигрупп, гидроксигруппы, карбоксильной группы,
С7-16аралкильных групп, тиоксогруппы, С2-7алканоильных групп,
С2-7тиоалканоильных групп, тиоформильной группы, аминогруппы,
С1-6алкиламиногрупп, ди(С1-6алкил)аминогрупп,
С1-6алкоксикарбонильных групп, карбамоильной группы,
С1-6алкилкарбамоильных групп, ди(С1-6алкил)карбамоильных групп,
тиокарбамоильной группы, С1-6алкилтиокарбамоильных групп,
ди(С1-6алкил)тиокарбамоильных групп,
С1-6алкоксикарбамоиламиногрупп,
С1-6алкоксикарбамоил(С1-6алкил)аминогрупп,
С2-7алканоиламиногрупп, С2-7алканоил(С1-6алкил)аминогрупп,
тио-С2-7алканоиламиногрупп, тио-С2-7алканоил(С1-6алкил)аминогрупп,
формиламиногруппы, формил(С1-6алкил)аминогрупп,
тиоформиламиногруппы, тиоформил(С1-6алкил)аминогрупп,
С2-7алканоилоксигрупп, формилоксигруппы,
С1-6алкоксикарбонилоксигрупп, карбамоилоксигруппы,
С1-6алкилкарбамоилоксигрупп, ди(С1-6алкил)карбамоилоксигрупп,
аминокарбониламиногруппы, (С1-6алкил)аминокарбониламиногрупп,
ди(С1-6алкил)аминокарбониламиногрупп,
аминокарбонил(С1-6алкил)аминогрупп,
(С1-6алкил)аминокарбонил(С1-6алкил)аминогрупп,
ди(С1-6алкил)аминокарбонил(С1-6алкил)аминогрупп,
меркаптогруппы, С1-6алкилтиогрупп, С1-6алкилсульфинильных групп,
С1-6алкилсульфонильных групп, аминосульфонильной группы,
С1-6алкиламиносульфонильных групп,
ди(С1-6алкил)аминосульфонильных групп,
С1-6алкилсульфониламиногрупп,
С1-6алкилсульфонил(С1-6алкил)аминогрупп,
аминосульфониламиногруппы, С1-6алкиламиносульфониламиногрупп,
ди(С1-6алкил)аминосульфониламиногрупп,
аминосульфонил(С1-6алкил)аминогрупп,
С1-6алкиламиносульфонил(С1-6алкил)аминогрупп и
ди(С1-6алкил)аминосульфонил(С1-6алкил)аминогрупп; или
N-оксид или S-оксид данного соединения; их соль; или
сольват описанного выше соединения.
7. Соединение по любому из пп.1-3, где R16 и R17, каждый, представляет моноциклическую или полициклическую ароматическую углеводородную группу, имеющую 6-14 атомов углерода, или гетероциклическую группу (где эта углеводородная группа или гетероциклическая группа может иметь 1-3 заместителя, выбранных из атомов галогена, С1-6алкильных групп,
С1-6алкоксигрупп, С2-6алкенильных групп, формильной группы,
С2-6алканоильных групп, карбоксильной группы,
карбоксиамино-С1-6алкильных групп,
С1-6алкоксикарбониламино-С1-6алкильных групп,
оксогруппы, нитрогруппы, цианогруппы, амидиногруппы,
С2-7алкенилоксигрупп, гидроксигруппы, тиоксогруппы, аминогруппы,
С1-6алкиламиногрупп, ди(С1-6алкил)аминогрупп,
С1-6алкоксикарбонильных групп, карбамоильной группы,
С1-6алкилкарбамоильных групп, ди(С1-6алкил)карбамоильных групп,
тиокарбамоильной группы, С1-6алкилтиокарбамоильных групп,
ди(С1-6алкил)тиокарбамоильных групп, меркаптогруппы,
С1-6алкилтиогрупп, С1-6алкилсульфинильных групп и
С1-6алкилсульфонильных групп);
и R15 представляет гетероциклическую группу (где гетероциклическая группа может быть замещена атомом галогена,
С1-6алкильной группой, С1-6алкоксигруппой,
С2-6алкенильной группой, С2-6алкенилоксигруппой, гидроксигруппой,
карбоксильной группой, карбокси-С1-6алкильной группой,
С1-6алкоксикарбонил-С1-6алкильной группой,
С1-6алкоксикарбонил-С2-6алкенильной группой,
гидроксил-С1-6алкильной группой,
С6-14ароматический углеводородсульфонил-С1-6алкильной группой,
гетероциклил-С1-6алкиламиногруппой, гетероциклической группой,
гетероциклил-С1-6алкильной группой,
С6-14ароматической углеводородной группой,
С6-14ароматический углеводород-С1-6алкильной группой,
С6-14ароматический углеводород-тио-С1-6алкильной группой,
азидо-(С1-6алкил)группой, амино-С1-6алкильной группой,
С1-6алкиламино-С1-6алкильной группой,
ди-С1-6алкиламино-С1-6алкильной группой,
гидроксил-С1-6алкиламино-С1-8алкильной группой,
С1-6алкокси-С1-6алкиламино-С1-6алкильной группой,
(гидрокси-С1-6алкил)(С1-6алкокси-С1-6алкил)амино-С1-6алкильной группой,
С2-6алканоиламино-С1-6алкильной группой,
С6-14ароматический углеводород-сульфониламино-С1-6алкильной группой,
С1-6алкоксикарбониламино-С1-6алкильной группой,
карбамоиламино-С1-6алкильной группой,
N-алкилкарбамоиламино-С1-6алкильной группой,
N,N-диалкилкарбамоиламино-С1-6алкильной группой,
аминосульфониламино-С1-6алкильной группой,
N-алкилсульфониламино-С1-6алкильной группой,
N,N-диалкилсульфониламино-С1-6алкильной группой,
С6-14ароматический углеводород-С1-6алкиламиногруппой,
гетероциклил-С1-6алкиламиногруппой,
карбамоилокси-С1-6алкильной группой,
N-алкилкарбамоилокси-С1-6алкильной группой,
N,N-диалкилкарбамоилокси-С1-6алкильной группой,
С6-14ароматический углеводород-С1-6алкилкарбамоилокси-С1-6алкильной группой,
С1-6алкоксикарбонилокси-С1-6алкильной группой,
С6-14ароматический углеводород-оксикарбонилокси-С1-6алкильной группой,
С6-14ароматический углеводород-сульфониламино-С1-6алканоиламино-С1-6алкильной группой,
С1-6алкоксикарбониламино-С1-6алкиламиногруппой,
амино-С1-6алкиламиногруппой, С1-6алкиламино-С1-6алкиламиногруппой,
ди(С1-6алкил)амино-С1-6алкиламиногруппой,
карбоксиамино-С1-6алкильной группой,
С1-6алкоксикарбониламино-С1-6алкильной группой,
С1-6алкилсульфониламино-С1-6алкильной группой,
амино-С1-6алкилкарбониламино-С1-6алкильной группой,
N-С1-6алкиламино-С1-6алкилкарбониламино-С1-6алкильной группой,
N,N-ди-С1-6алкиламино-С1-6алкилкарбониламино-С1-6алкильной группой,
гетероциклилкарбонильной группой,
гетероциклилкарбониламиногруппой,
С6-14ароматический углеводородкарбонильной группой,
С6-14ароматической карбониламиногруппой,
гетероциклил-С1-6алкилкарбониламино-С1-6алкильной группой,
гетероциклил-С2-6алкенилкарбониламино-С1-6алкильной группой,
С6-14ароматический углеводородалкенилкарбониламино-С1-6алкильной группой,
С6-14ароматический углеводородкарбониламино-С1-6алкильной группой,
гетероциклилкарбониламино-С1-6алкильной группой,
С1-6алкоксиоксалиламино-С1-6алкильной группой,
карбамоильной группой, N-С1-6алкилкарбамоильной группой,
N,N-ди-С1-6алкилкарбамоильной группой,
С1-6алкил-С3-8циклоалкилкарбамоильной группой,
С3-8циклоалкил-С1-6алкилкарбамоильной группой,
гетероциклилкарбамоильной группой,
С1-6ароматической карбамоильной группой,
гетероциклилкарбонилгидразонометильной группой,
С6-14ароматический углеводородкарбонилгидразонометильной группой,
С1-6алкилтио-С1-6алкилкарбамоильной группой,
С1-6алкилсульфинил-С1-6алкилкарбамоильной группой,
С1-6алкилсульфонил-С1-6алкилкарбамоильной группой,
гидроксиаминокарбонильной группой,
гидразинокарбонильной группой или
N-С1-6алкилгидразинокарбонильной группой,
тиоформиламино-С6-14ароматический углеводородтиокарбониламино-С1-6алкильной группой
тиоформил(С1-6алкил)амино-С6-14ароматический углеводородтиокарбониламино-С1-6алкильной группой,
формиламино-С6-14ароматический углеводородкарбониламино-С1-6алкильной группой,
формил-С1-6алкиламино-С6-14ароматический углеводородкарбониламино-С1-6алкильной группой,
С1-6алканоилгетероциклкарбониламино-С1-6алкильной группой,
ди(С2-6алканоил)амино(С1-6алкил)группой,
ди(С1-6алкоксикарбонил)амино-С1-6алкильной группой,
С1-6алкилгетероциклкарбонильной группой,
С3-7циклоалкил-С1-6алкиламинокарбонильной группой,
С1-6алкоксиаминокарбонильной группой,
(гидрокси)(С1-6алкил)аминокарбонильной группой,
(С1-6алкокси)(С1-6алкил)аминокарбонильной группой,
N’-С1-6алкилгидразинокарбонильной группой,
N’,N’-ди-С1-6алкилгидразинокарбонильной группой,
N,N’-ди-С1-6алкилгидразинокарбонильной группой,
N,N’,N’-три-С1-6алкилгидразинокарбонильной группой,
N’-(гетероциклкарбонил)гидразинокарбонильной группой,
формильной группой, гидроксилиминогруппой,
С1-6алкоксииминогруппой,
бис(С1-6алкокси-С1-6алкил)амино-С1-6алкильной группой,
гидрокси-С1-6алкилгетероциклической группой,
С1-6алкокси-С1-6алкилгетероциклической группой,
С1-6алкоксикарбониламино-С1-6алкилгетероциклической группой,
амино-С1-6алкилгетероциклической группой,
N-С1-6алкиламино-С1-6алкилгетероциклической группой,
N,N-ди-С1-6алкиламино-С1-6алкилгетероциклической группой,
гидроксигетероциклической группой,
С1-6алкоксигетероциклической группой,
карбокси-С2-5алкенильной группой или
оксогруппой,
(где вышеуказанная С6-14ароматическая углеводородная группа или гетероциклическая группа может быть замещена атомом галогена, С1-6алкильной группой, С1-6алкоксигруппой,
С2-6алкенильной группой, формильной группой,
С2-6алканоильной группой, карбоксильной группой,
карбоксиамино-С1-6алкильной группой,
С1-6алкоксикарбониламино-С1-6алкильной группой, оксогруппой,
нитрогруппой, цианогруппой, амидиногруппой,
С2-6алкенилоксигруппой, гидроксигруппой, тиоксогруппой,
аминогруппой, С1-6алкиламиногруппой, ди-С1-6алкиламиногруппой,
амино-С1-6алкильной группой, С1-6алкоксикарбонильной группой,
карбамоильной группой, С1-6алкилкарбамоильной группой,
ди-С1-6алкилкарбамоильной группой, тиокарбамоильной группой,
С1-6алкилтиокарбамоильной группой,
ди(С1-6алкил)тиокарбамоильной группой,
С2-7алканоиламиногруппой, С2-7алканоил(С1-6алкил)аминогруппой,
тио(С2-7алканоил)аминогруппой,
тио(С2-7алканоил)(С1-6алкил)аминогруппой,
формиламиногруппой, формил(С1-6алкил)аминогруппой,
тиоформиламиногруппой, тиоформил(С1-6алкил)аминогруппой,
С2-7алканоилоксигруппой, формилоксигруппой, меркаптогруппой,
С1-6алкилтиогруппой, С1-6алкилсульфинильной группой,
С1-6алкилсульфонильной группой, аминосульфонильной группой,
С1-6алкиламиносульфонильной группой,
ди(С1-6алкил)аминосульфонильной группой,
С1-6алкилсульфониламиногруппой или
С1-6алкилсульфонил(С1-6алкил)аминогруппой); или
N-оксид или S-оксид данного соединения; их соль; или
сольват описанного выше соединения.
8. Лекарственное средство, содержащее, в качестве активного ингредиента, соединение по любому из пп.1-7 или N-оксид или S-оксид данного соединения, их соль или сольват описанного выше соединения.
9. Лекарственное средство по п.8, которое применяют для предупреждения или лечения заболевания, являющегося результатом аномального продуцирования или секреции β-амилоида.
10. Лекарственное средство по п.8, которое применяют для предупреждения или лечения болезни Альцгеймера или синдрома Дауна.
11. Фармацевтическая композиция, содержащая соединение по любому из пп.1-7 или N-оксид или S-оксид данного соединения, их соль или сольват описанного выше соединения, и фармацевтически приемлемый носитель.
12. Применение соединения по любому из пп.1-7 или N-оксида или S-оксида данного соединения, их соли или сольвата описанного выше соединения, для изготовления лекарственного средства.
13. Применение по п.12, где лекарственное средство применяют для предупреждения или лечения заболевания, являющегося результатом аномального продуцирования или секреции β-амилоидного белка.
14. Применение по п.12, где лекарственное средство применяют для предупреждения или лечения болезни Альцгеймера или синдрома Дауна.
15. Способ лечения заболевания, являющегося результатом аномального продуцирования или секреции β-амилоида, включающий введение эффективного количества соединения по любому из пп.1-7 или N-оксида или S-оксида данного соединения, их соли или сольвата описанного выше соединения.
16. Способ по п.15, где заболевание, являющееся результатом аномального продуцирования или секреции β-амилоидного белка, представляет собой болезнь Альцгеймера или синдром Дауна.
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JPWO2003055850A1 (ja) 2005-05-12
CN1585746A (zh) 2005-02-23
US7399775B2 (en) 2008-07-15
JP4329905B2 (ja) 2009-09-09
KR100927304B1 (ko) 2009-11-18
TW200306810A (en) 2003-12-01
CN100562516C (zh) 2009-11-25
US20070293495A1 (en) 2007-12-20
US20050234109A1 (en) 2005-10-20
KR20040068978A (ko) 2004-08-02
RU2304140C2 (ru) 2007-08-10
WO2003055850A1 (fr) 2003-07-10
EP1466898A4 (en) 2005-12-07
CA2471943A1 (en) 2003-07-10
CA2471943C (en) 2011-09-20
AU2002367147A1 (en) 2003-07-15
HK1071354A1 (en) 2005-07-15
TWI330176B (en) 2010-09-11
EP1466898A1 (en) 2004-10-13

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