RU2004130455A - Производные аминоспиртов - Google Patents

Производные аминоспиртов Download PDF

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Publication number
RU2004130455A
RU2004130455A RU2004130455/04A RU2004130455A RU2004130455A RU 2004130455 A RU2004130455 A RU 2004130455A RU 2004130455/04 A RU2004130455/04 A RU 2004130455/04A RU 2004130455 A RU2004130455 A RU 2004130455A RU 2004130455 A RU2004130455 A RU 2004130455A
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RU
Russia
Prior art keywords
salt
formula
compound
tetrahydro
represents hydrogen
Prior art date
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RU2004130455/04A
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English (en)
Inventor
Коудзи ХАТТОРИ (JP) ХАТТОРИ Коудзи (JP)
Коудзи Хаттори
Ясуе ТОМИСИМА (JP) ТОМИСИМА Ясуе (JP)
Ясуе ТОМИСИМА
Ютака НАКАДЗИМА (JP) НАКАДЗИМА Ютака (JP)
Ютака НАКАДЗИМА
Масаси ИМАНИСИ (JP) ИМАНИСИ Масаси (JP)
Масаси ИМАНИСИ
Original Assignee
Фудзисава Фармасьютикал Ко.,Лтд. (Jp) Фудзисава Фармасьютикал Ко.,Лтд. (Jp)
Фудзисава Фармасьютикал Ко.,Лтд.
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Priority claimed from AUPS1104A external-priority patent/AUPS110402A0/en
Priority claimed from AU2003900127A external-priority patent/AU2003900127A0/en
Application filed by Фудзисава Фармасьютикал Ко.,Лтд. (Jp) Фудзисава Фармасьютикал Ко.,Лтд. (Jp), Фудзисава Фармасьютикал Ко.,Лтд. filed Critical Фудзисава Фармасьютикал Ко.,Лтд. (Jp) Фудзисава Фармасьютикал Ко.,Лтд. (Jp)
Publication of RU2004130455A publication Critical patent/RU2004130455A/ru

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Claims (11)

1. Соединение формулы [I]
Figure 00000001
где
Figure 00000002
представляет собой
Figure 00000003
каждый из R1 и R5 независимо представляет собой водород, галоген, низший алкил, моно (или ди- или три)галоген(низший)алкил или циано;
R2 представляет собой водород или защитную группу амина;
Х представляет собой связь, -О-, -О-СН2-,
Figure 00000004
-(CH2)q- (где q равен от 1 до 3);
-СН=СН-, -С≡С-, -NH-, -S- или -SO2-,
Y представляет собой
Figure 00000005
Figure 00000006
или
Figure 00000007
,
где Z представляет собой связь, -O-(CH2)m- (где m равен от 1 до 4), низший алкилен или низший алкенилен;
R3 представляет собой низший алканоил, карбокси, низший алкоксикарбонил, карбамоил, (низший алкилсульфонил)карбамоил, (фенилсульфонил)карбамоил, (бензилсульфонил)карбамоил или тетразолил; и
R4 представляет собой водород, галоген, гидрокси, фенокси, низший алкил, низший алкокси, цикло(низший)алкилокси, 3,4,5,6-тетрагидро-2Н-пиранилокси, фенокси, нитро, циано или
Figure 00000008
,
где R6 представляет собой водород или низший алкил; и
R7 представляет собой водород, низший алкил, низший алканоил, низший алкоксикарбонил, бензилоксикарбонил, бензоил, фуроил, низший алкилкарбамоил, фенилкарбамоил, низший алкилсульфонил, 3,4,5,6-тетрагидро-2Н-пиранил или фенил, или
R6 и R7 объединены, образуя вместе с атомом азота пирролидино или пиперидино, которые могут быть замещены оксогруппой; и
n равно 0, 1 или 2,
или его соль.
2. Соединение по п.1,
где R1 представляет собой водород или галоген;
R2 представляет собой водород;
Х представляет собой связь, -О-, -О-СН2-;
Figure 00000009
-(CH2)q- (где q равен 1 или 2);
-СН=СН-, -С≡С-, -NH-, -S- или -SO2-,
Y представляет собой
Figure 00000005
Figure 00000006
или
Figure 00000007
,
где Z представляет собой связь, -O-(CH2)m- (где m равен от 1 до 4), низший алкилен или низший алкенилен;
R3 представляет собой низший алканоил, карбокси, низший алкоксикарбонил, карбамоил, (низший алкилсульфонил)карбамоил, (фенилсульфонил)карбамоил, (бензилсульфонил)карбамоил или тетразолил; и
R4 представляет собой водород, галоген, гидрокси, фенокси, низший алкил, низший алкокси, цикло(низший)алкилокси, 3,4,5,6-тетрагидро-2Н-пиранилокси, фенокси, нитро, циано или
Figure 00000008
,
где R6 представляет собой водород или низший алкил; и
R7 представляет собой водород, низший алкил, низший алканоил, низший алкоксикарбонил, бензилоксикарбонил, бензоил, фуроил, низший алкилкарбамоил, фенилкарбамоил, низший алкилсульфонил, 3,4,5,6-тетрагидро-2Н-пиранил или фенил, или
R6 и R7 объединены, образуя вместе с атомом азота пирролидино или пиперидино, которые могут быть замещены оксогруппой; и
n равно 0, 1 или 2.
3. Соединение по п.2, где
Figure 00000010
представляет собой
Figure 00000011
R1 представляет собой галоген,
R5 представляет собой водород,
R2 представляет собой водород,
Х представляет собой связь, -О- или -О-СН2,
Y представляет собой
Figure 00000012
или
Figure 00000013
где Z представляет собой связь, -O-(CH2)m- (где m равен 1 или 2), или низший алкенилен;
R3 представляет собой низший алканоил, карбокси, низший алкоксикарбонил, карбамоил или тетразолил; и
R4 представляет собой водород или низший алкокси; и
n равно 1 или 2.
4. Соединение по п.3,
где R1 представляет собой хлор;
Х представляет собой связь или -О-;
Y представляет собой
Figure 00000014
или
Figure 00000013
,
где Z представляет собой связь или низший алкенилен;
R3 представляет собой карбокси; и
R4 представляет собой водород или низший алкокси; и
n равно 1.
5. Соединение по п.4, представляющее собой
(1) 3-[[(7S)-7-[[(2R)-2-(3-хлорфенил)-2-гидроксиэтил]амино]-5,6,7,8-тетрагидро-2-нафталенил]окси]бензойную кислоту;
(2) 2-[[(7S)-7-[[(2R)-2-(3-хлорфенил)-2-гидроксиэтил]амино]-5,6,7,8-тетрагидро-2-нафталенил]окси]никотиновую кислоту;
(3) 3-[2-[[(7S)-7-[[(2R)-2-(3-хлорфенил)-2-гидроксиэтил]амино]-5,6,7,8-тетрагидро-2-нафталенил]окси]-3-пиридил]-2-пропеновую кислоту;
(4) 3-[6-[[(7S)-7-[[(2R)-2-(3-хлорфенил)-2-гидроксиэтил]амино]-5,6,7,8-тетрагидро-2-нафталенил]окси]-3-пиридил]-2-пропеновую кислоту;
(5) 4-[(7S)-7-[[(2R)-2-(4-хлорфенил)-2-гидроксиэтил]амино]-5,6,7,8-тетрагидро-2-нафталенил]бензойную кислоту;
(6) 4-[(7S)-7-[[(2R)-2-(4-хлорфенил)-2-гидроксиэтил]амино]-5,6,7,8-тетрагидро-2-нафталенил]-2-метоксибензойную кислоту; или
(7) 5-[[(7S)-7-[[(2R)-2-(4-хлорфенил)-2-гидроксиэтил]амино]-5,6,7,8-тетрагидро-2-нафталенил]окси]-2-метоксибензойную кислоту;
или ее соль.
6. Способ получения соединения по п.1 или его соли, включающий
(i) взаимодействие соединения [II] формулы
Figure 00000015
где каждый из
Figure 00000002
, R1 и R5 является таким, как определено в п.1, с соединением [III] формулы
Figure 00000016
где каждый из R2, X, Y и n является таким, как определено в п.1, или его солью с образованием соединения [I] формулы
Figure 00000017
где каждый из
Figure 00000002
, R1, R5, R2, X, Y и n является таким, как определено в п.1, или его соли,
(ii) введение соединения [Ia] формулы
Figure 00000018
где каждый из
Figure 00000002
, R1, R5, X, Y и n является таким, как определено в п.1, и Ra 2 представляет собой защитную группу амина, или его соли в реакцию элиминирования защитной группы амина с получением соединения [Ib] формулы
Figure 00000019
где каждый из
Figure 00000002
, R1, R5, X, Y и n является таким, как определено в п.1, или его соли,
(iii) взаимодействие соединения [IV] формулы
Figure 00000020
где каждый из
Figure 00000002
, R1, R5, R2 и n является таким, как определено в п.1, или его соли, с соединением [V] формулы
(HO)2B-Y [V]
где Y является таким, как определено в п.1, или его солью с получением соединения [Ic] формулы
Figure 00000021
где каждый из
Figure 00000002
, R1, R5, R2, Y и n является таким, как определено в п.1, или его соли,
(iv) взаимодействие соединения [IV] формулы
Figure 00000022
где каждый из
Figure 00000002
, R1, R5, R2 и n является таким, как определено в п.1, или его соли, с соединением [VI] формулы
X1-Y [VI]
где Y является таким, как определено в п.1, и Х1 представляет собой уходящую группу, или его солью, с получением соединения [Ic] формулы
Figure 00000021
где каждый из
Figure 00000002
, R1, R5, R2, Y и n является таким, как определено в п.1, или его соли,
(v) взаимодействие соединения [VII] формулы
Figure 00000023
где каждый из
Figure 00000024
, R1, R5, R2 и n является таким, как определено в п.1, Х2 представляет собой уходящую группу, или его соли, с соединением [V] формулы
(HO)2B-Y [V]
где Y является таким, как определено в п.1, или его солью с получением соединения [Id] формулы
Figure 00000025
где каждый из
Figure 00000002
, R1, R5, R2, Y и n является таким, как определено в п.1, или его соли.
7. Фармацевтическая композиция, содержащая в качестве активного ингредиента соединение по п.1 или его фармацевтически приемлемую соль в смеси с фармацевтическими приемлемыми носителями или эксципиентами.
8. Применение соединения по п.1 или его фармацевтически приемлемой соли для изготовления лекарственного средства.
9. Соединение по п.1 или его фармацевтически приемлемая соль для применения в качестве лекарственного средства.
10. Соединение по п.1 или его фармацевтически приемлемая соль для применения в качестве селективных агонистов β3 адренергического рецептора.
11. Способ профилактики и/или терапевтического лечения поллакиурии, недержания мочи, ожирения или диабета, включающий введение соединения по п.1 или его фармацевтически приемлемой соли человеку или животному.
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