RU2002123882A - Производные индола, способ их получения и их применение - Google Patents

Производные индола, способ их получения и их применение

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Publication number
RU2002123882A
RU2002123882A RU2002123882/04A RU2002123882A RU2002123882A RU 2002123882 A RU2002123882 A RU 2002123882A RU 2002123882/04 A RU2002123882/04 A RU 2002123882/04A RU 2002123882 A RU2002123882 A RU 2002123882A RU 2002123882 A RU2002123882 A RU 2002123882A
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RU
Russia
Prior art keywords
alkyl
substituted
cyano
alkoxy
hydroxy
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RU2002123882/04A
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English (en)
Other versions
RU2259998C2 (ru
Inventor
Казухико ТОРИСУ (JP)
Казухико ТОРИСУ
Каору КОБАЯСИ (JP)
Каору КОБАЯСИ
Фумио НАМБУ (JP)
Фумио НАМБУ
Original Assignee
Оно Фармасьютикал Ко., Лтд. (Jp)
Оно Фармасьютикал Ко., Лтд.
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Publication of RU2002123882A publication Critical patent/RU2002123882A/ru
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Publication of RU2259998C2 publication Critical patent/RU2259998C2/ru

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
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    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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    • A61K31/42—Oxazoles
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    • A61K31/423—Oxazoles condensed with carbocyclic rings
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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    • A61K31/5375—1,4-Oxazines, e.g. morpholine
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Claims (13)

1. Производное индола, представленное формулой (I)
Figure 00000001
где R1 представляет гидрокси, (С1-6)-алкокси или NR8R9, где R8 и R9, каждый независимо, представляет атом водорода, (С1-6)-алкил или SO2R13, где R13 представляет (С1-6)-алкил, насыщенное или ненасыщенное карбоциклическое кольцо (С3-15) или 4-15-членное гетероциклическое кольцо, содержащее 1-5 атомов азота, атомов серы и/или атомов кислорода;
R2 представляет атом водорода, (С1-6)-алкил, (С1-6)-алкокси, (С2-6)-алкоксиалкил, атом галогена, амино, тригалогенметил, циано, гидрокси, бензил или 4-метоксибензил;
R3 представляет атом водорода, (С1-6)-алкил, (С1-6)-алкокси, атом галогена, тригалогенметил, циано или гидрокси;
R4 и R5, каждый независимо, представляет атом водорода, (С1-6)-алкил, (С1-6)-алкокси, (С2-6)-алкоксиалкил, атом галогена, нитро, амино, тригалогенметил, циано или гидрокси;
D представляет простую связь, (С1-6)-алкилен, (С2-6)-алкенилен или (С1-6)-оксиалкилен;
в -G-R6:
1) G представляет простую связь, (С1-6)-алкилен, который может быть замещен 1-2 атомами кислорода и/или атомами серы, (С2-6)-алкенилен, который может быть замещен 1-2 атомами кислорода и/или атомами серы, где алкилен и алкенилен могут быть замещены гидрокси или (С1-4)-алкокси, -C(O)NH-, -NHC(O)-, -SO2NH-, -NHSO2- или диазо;
R6 представляет насыщенное или ненасыщенное карбоциклическое кольцо (С3-15) или 4-15-членное гетероциклическое кольцо, содержащее 1-5 атомов азота, атомов серы и/или атомов кислорода, где кольцо может быть замещено 1-5 заместителями, выбранными из (С1-6)-алкила, (С1-10)-алкокси, (С2-6)-алкоксиалкила, атома галогена, гидрокси, тригалогенметила, нитро, амино, фенила, фенокси, оксо, (С2-6)-ацила, (С1-6)-алкансульфонила и циано;
2) G и R6, взятые вместе, представляют (i) (C1-15)-алкил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, (ii) (С2-15)-алкенил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, или (iii) (C2-15)-алкинил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, где алкил, алкенил или алкинил могут быть замещены 1-12 заместителями, выбранными из числа (С1-6)-алкокси, атома галогена, гидрокси, циано, оксо и NR11R12, где R11 и R12, каждый независимо, представляет атом водорода, (С1-6)-алкил, (С2-6)-алкенил, фенил, бензоил, нафтил, фенил, замещенный (С1-6)-алкилом, или (С1-6)-алкил, замещенный фенилом или циано;
n=1-3;
m=1-3;
i=1-4;
Figure 00000002
Figure 00000003
представляет простую связь или двойную связь,
или его нетоксичная соль.
2. Производное индола по п.1, где D представляет простую связь, или его нетоксичная соль.
3. Производное индола по п.1, где D представляет (С1-6)-алкилен, или его нетоксичная соль.
4. Производное индола по п.1, где D представляет (С2-6)-алкенилен, или его нетоксичная соль.
5. Производное индола по п.1, где D представляет (С1-6)-оксиалкилен, или его нетоксичная соль.
6. Производное индола по п.1, где R6 представляет насыщенное или ненасыщенное карбоциклическое кольцо (С3-15), где кольцо может быть замещено 1-5 группами, выбранными из группы, состоящей из (С1-6)-алкила, (С1-10)-алкокси, (С2-6)-алкоксиалкила, атома галогена, тригалогенметила, гидрокси, нитро, амино, фенила, фенокси, оксо, (С2-6)-ацила, (С1-6)-алкансульфонила и циано, или его нетоксичная соль.
7. Производное индола по п.1, где R6 представляет 4-15-членное гетероциклическое кольцо, содержащее 1-5 атомов азота, атомов серы и/или атомов кислорода, где кольцо может быть замещено 1-5 группами, выбранными из группы, состоящей из (С1-6)-алкила, (С1-10)-алкокси, (С2-6)-алкоксиалкила, атома галогена, тригалогенметила, гидрокси, нитро, амино, фенила, фенокси, оксо, (С2-6)-ацила, (С1-6)-алкансульфонила и циано, или его нетоксичная соль.
8. Производное индола по п.1, где G и R6, взятые вместе, представляют (i) (C1-15)-алкил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, (ii) (С2-15)-алкенил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, или (iii) (С2-15)-алкинил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, где алкил, алкенил или алкинил могут быть замещены 1-12 заместителями, выбранными из группы, состоящей из (С1-6)-алкокси, атома галогена, гидрокси, циано, оксо и NR11R12, где R11 и R12, каждый независимо, представляет атом водорода, (С1-6)-алкил, (С2-6)-алкенил, фенил, бензоил, нафтил, фенил, замещенный (С1-6)-алкилом, или (С1-6)-алкил, замещенный фенилом или циано, или его нетоксичная соль.
9. Способ получения карбоновой кислоты, представленной формулой (Iа)
Figure 00000004
где все символы имеют значения, указанные ниже,
включающий реакцию удаления защитной группы соединения, представленного формулой (IV)
Figure 00000005
где R20 представляет аллильную или бензильную группу, и другие символы имеют значения, указанные в п.1.
10. Способ получения соединения, представленного формулой (Ib)
Figure 00000006
где все символы имеют значения, указанные ниже,
включающий реакцию этерификации карбоновой кислоты, представленной формулой (Iа)
Figure 00000007
где все символы имеют значения, указанные ниже, спиртом, представленным формулой
R10-OH, (III)
где R10 представляет (С1-6)-алкил,
с последующей, необязательно, реакцией удаления защитной группы.
11. Способ получения соединения, представленного формулой (Iс)
Figure 00000008
где все символы имеют значения, указанные ниже,
включающий реакцию амидирования карбоновой кислоты, представленной формулой (Iа)
Figure 00000009
где все символы имеют значения, указанные в п.1,
амином, представленным формулой (II)
NR10R11, (II)
где все символы имеют значения, указанные в п.1,
с последующей, необязательно, реакцией удаления защитной группы.
12. Антагонист DP-рецептора, содержащий в качестве активного ингредиента производное индола формулы (I) или его нетоксичную соль.
13. 2-Метилиндол-4-уксусная кислота.
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