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RU2009108275A - Соединение сульфонамида или его соль - Google Patents

Соединение сульфонамида или его соль Download PDF

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Publication number
RU2009108275A
RU2009108275A RU2009108275/04A RU2009108275A RU2009108275A RU 2009108275 A RU2009108275 A RU 2009108275A RU 2009108275/04 A RU2009108275/04 A RU 2009108275/04A RU 2009108275 A RU2009108275 A RU 2009108275A RU 2009108275 A RU2009108275 A RU 2009108275A
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RU
Russia
Prior art keywords
methylphenyl
substituted
lower alkyl
sulfonyl
glycyl
Prior art date
Application number
RU2009108275/04A
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English (en)
Other versions
RU2425029C2 (ru
Inventor
Хидеки КУБОТА (JP)
Хидеки КУБОТА
Сусуму ТОДА (JP)
Сусуму ТОДА
Иссеи ЦУКАМОТО (JP)
Иссеи ЦУКАМОТО
Юта ФУКУДА (JP)
Юта ФУКУДА
Рютаро ВАКАЯМА (JP)
Рютаро ВАКАЯМА
Казуки ОНО (JP)
Казуки ОНО
Тору ВАТАНАБЕ (JP)
Тору ВАТАНАБЕ
Хиденори АЗАМИ (JP)
Хиденори АЗАМИ
Original Assignee
Астеллас Фарма Инк. (Jp)
Астеллас Фарма Инк.
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Application filed by Астеллас Фарма Инк. (Jp), Астеллас Фарма Инк. filed Critical Астеллас Фарма Инк. (Jp)
Publication of RU2009108275A publication Critical patent/RU2009108275A/ru
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Publication of RU2425029C2 publication Critical patent/RU2425029C2/ru

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    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • A61K31/19—Carboxylic acids, e.g. valproic acid
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    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
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    • A61K31/4015—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 having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
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    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

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Abstract

1. Антагонист рецептора EP1, включающий в качестве активного ингредиента соединение сульфонамида, представленное формулой (I), или его фармацевтически приемлемую соль: ! [хим. 19] ! ! в которой ! кольцо A: бензольное кольцо, циклоалкановое кольцо или гетероароматическое кольцо, ! L1: простая связь или низший алкилен, ! L2: низший алкилен, ! R1-R4: одинаковые или различные, причем каждый обозначает R0, галоген, галоген-низший алкил, -OR0, -O-галоген-низший алкил, -S(O)n-низший алкил, -CN, -NO2, азотсодержащую гетероциклическую группу, циклоалкил, -NH-CO-низший алкил, -NH-CO-N(R00)2, -NH-CO-азотсодержащую гетероциклическую группу, -CO2R0, -CON(R0)2, -СО-низший алкил, -низший алкилен-OR0, -низший алкилен-CO2R0, арил, который может быть замещен, гетероарил, который может быть замещен, -О-арил, который может быть замещен, -О-бензил или -О-гетероарил, который может быть замещен, или ! когда R1 и R2, и R3 и R4, каждый, находятся на смежных атомах углерода бензольного кольца или кольца A, они могут вместе с кольцевым атомом, к которому они присоединены, образовывать 5-7-членное циклоалкеновое кольцо, бензольное кольцо или гетероцикл, которые могут быть замещены группой, выбранной из следующей группы G1, ! группа G1: низший алкил, оксо, -OR0, -низший алкилен-OR0 и -СО-низший алкил, ! R0: одинаковые или различные, обозначают, каждый, Н или низший алкил, ! R00: Н или низший алкил, который может быть замещен группой -OR0, ! n: 0, 1 или 2, ! RA: R0, ! RB: R0, -низший алкилен-арил, который может быть замещен, -низший алкилен-гетероарил, который может быть замещен, -низший алкилен-O-арил, который может быть замещен, или -низший алкилен-O-гетероарил, который может быть замещен, или ! RA и RB могут вместе с атомом азота, к которому

Claims (18)

1. Антагонист рецептора EP1, включающий в качестве активного ингредиента соединение сульфонамида, представленное формулой (I), или его фармацевтически приемлемую соль:
[хим. 19]
Figure 00000001
в которой
кольцо A: бензольное кольцо, циклоалкановое кольцо или гетероароматическое кольцо,
L1: простая связь или низший алкилен,
L2: низший алкилен,
R1-R4: одинаковые или различные, причем каждый обозначает R0, галоген, галоген-низший алкил, -OR0, -O-галоген-низший алкил, -S(O)n-низший алкил, -CN, -NO2, азотсодержащую гетероциклическую группу, циклоалкил, -NH-CO-низший алкил, -NH-CO-N(R00)2, -NH-CO-азотсодержащую гетероциклическую группу, -CO2R0, -CON(R0)2, -СО-низший алкил, -низший алкилен-OR0, -низший алкилен-CO2R0, арил, который может быть замещен, гетероарил, который может быть замещен, -О-арил, который может быть замещен, -О-бензил или -О-гетероарил, который может быть замещен, или
когда R1 и R2, и R3 и R4, каждый, находятся на смежных атомах углерода бензольного кольца или кольца A, они могут вместе с кольцевым атомом, к которому они присоединены, образовывать 5-7-членное циклоалкеновое кольцо, бензольное кольцо или гетероцикл, которые могут быть замещены группой, выбранной из следующей группы G1,
группа G1: низший алкил, оксо, -OR0, -низший алкилен-OR0 и -СО-низший алкил,
R0: одинаковые или различные, обозначают, каждый, Н или низший алкил,
R00: Н или низший алкил, который может быть замещен группой -OR0,
n: 0, 1 или 2,
RA: R0,
RB: R0, -низший алкилен-арил, который может быть замещен, -низший алкилен-гетероарил, который может быть замещен, -низший алкилен-O-арил, который может быть замещен, или -низший алкилен-O-гетероарил, который может быть замещен, или
RA и RB могут вместе с атомом азота, к которому они присоединены, образовывать азотсодержащий гетероцикл.
2. Антагонист рецептора EP1 по п.1, в котором RA обозначает Н и RB обозначает -низший алкилен-арил, который может быть замещен, -низший алкилен-гетероарил, который может быть замещен, -низший алкилен-O-арил, который может быть замещен, или -низший алкилен-O-гетероарил, который может быть замещен.
3. Соединение сульфонамида, представленное формулой (II), или его фармацевтически приемлемая соль:
[хим. 20]
Figure 00000002
в которой
кольцо A: бензольное кольцо, циклоалкановое кольцо или гетероароматическое кольцо,
L1: простая связь или низший алкилен,
L2: низший алкилен,
R1-R4: одинаковые или различные, причем каждый обозначает R0, галоген, галоген-низший алкил, -OR0, -O-галоген-низший алкил, -S(O)n-низший алкил, -CN, -NO2, азотсодержащую гетероциклическую группу, циклоалкил, -NH-CO-низший алкил, -NH-CO-N(R00)2, -NH-CO-азотсодержащую гетероциклическую группу, -CO2R0, -CON(R0)2, -СО-низший алкил, -низший алкилен-OR0, -низший алкилен-CO2R0, арил, который может быть замещен, гетероарил, который может быть замещен, -О-арил, который может быть замещен, -О-бензил или -О-гетероарил, который может быть замещен, или
когда R1 и R2, и R3 и R4, каждый, находятся на смежных атомах углерода бензольного кольца или кольца A, они могут вместе с кольцевым атомом, к которому они присоединены, образовывать 5-7-членное циклоалкеновое кольцо, бензольное кольцо или гетероцикл, которые могут быть замещены группой, выбранной из следующей группы G1,
группа G1: низший алкил, оксо, -OR0, -низший алкилен-OR0 и -СО-низший алкил,
R0: одинаковые или различные, обозначают, каждый, Н или низший алкил,
R00: Н или низший алкил, который может быть замещен группой -OR0,
n: 0, 1 или 2,
L3: низший алкилен,
X: простая связь или -O-,
кольцо B: бензольное кольцо или гетероароматическое кольцо,
R5 и R6: одинаковые или различные, каждый из которых обозначает R0, галоген, галоген-низший алкил, -OR0, -O-галоген-низший алкил, -CN или -NO2,
Y: простая связь, низший алкилен, низший алкенилен или -O-низший алкилен-,
Z: -CO2H или биологический эквивалент, -CONR7R8 или азотсодержащая гетероциклическая группа, которая может быть замещена группой, выбранной из группы G1,
R7 и R8: одинаковые или различные, обозначают, каждый, Н или низший алкил, который может быть замещен группой, выбранной из следующей группы G2, и
группа G2: -OR0, -N(R0)2, -CO2R0 и азотсодержащая гетероциклическая группа,
при условии, что исключены 4-({[N-[(4-фторфенил)сульфонил]-N-(2-метоксифенил)глицил]амино}метил)метилбензоат и N2-[(4-хлорфенил)сульфонил]-N2-(2,5-дифторфенил)-N-[4-(1,2,3-тиадиазол-4-ил)бензил]-D-аланинамид.
4. Соединение или его фармацевтически приемлемая соль по п.3, в котором L1 обозначает простую связь.
5. Соединение или его фармацевтически приемлемая соль по п.4, в котором кольцо A представляет собой бензольное кольцо.
6. Соединение или его фармацевтически приемлемая соль по п.5, в котором X обозначает простую связь.
7. Соединение или его фармацевтически приемлемая соль по п.6, в котором L2 и L3 оба обозначают метилен.
8. Соединение или его фармацевтически приемлемая соль по п.7, в котором Z обозначает -CO2H или биологический эквивалент.
9. Соединение сульфонамида, представленное формулой (II-A), или его фармацевтически приемлемая соль:
[хим. 21]
Figure 00000003
в которой
R10-R12: одинаковые или различные, обозначают, каждый, галоген, низший алкил, галоген-низший алкил, -OR0, -O-галоген-низший алкил или -CN,
R13: R0, галоген, галоген-низший алкил, -OR0, -O-галоген-низший алкил или -CN,
кольцо B: бензольное кольцо или гетероароматическое кольцо,
R14: R0, галоген или -OR0,
R0: одинаковые или различные, обозначают, каждый, Н или низший алкил,
Y1: простая связь, низший алкилен, низший алкенилен или -O-низший алкилен-, и
Z1: -CO2H или биологический эквивалент.
10. Соединение или его фармацевтически приемлемая соль по п.3, которое выбрано из группы, состоящей из следующих соединений:
4-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]бензойная кислота,
3-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]бензойная кислота,
3-[({N-(3-хлор-2-метилфенил)-N-[(4-хлорфенил)сульфонил]глицил}амино)метил]бензойная кислота,
3-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]феноксиуксусная кислота,
4-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]-N-(метилсульфонил)бензамид,
3-[({N-(3-хлор-2-метилфенил)-N-[(4-цианофенил)сульфонил]глицил}амино)метил]бензойная кислота,
3-{[(N-(3-хлор-2-метилфенил)-N-{[4-(трифторметил)фенил]сульфонил}глицил)амино]метил}бензойная кислота,
4-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]-2-метокси-N-(метилсульфонил)бензамид,
3-[({N-(2,3-дихлорфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]бензойная кислота,
3-[({N-(3-хлор-2-метоксифенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]бензойная кислота,
3-[({N-(3-бром-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]бензойная кислота,
3-[({N-(3-хлор-2-метилфенил)-N-[(4-этилфенил)сульфонил]глицил}амино)метил]бензойная кислота,
3-[({N-(3-хлор-2-этилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]бензойная кислота,
3-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]коричная кислота,
3-{3-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]фенил}пропионовая кислота,
5-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]тиофен-3-карбоновая кислота,
3-[({N-(3-хлор-2-этилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]коричная кислота,
3-{[(N-(3-хлор-2-метилфенил)-N-{[4-(трифторметил)фенил]сульфонил}глицил)амино]метил}коричная кислота,
3-[({N-(3-хлор-2-метилфенил)-N-[(4-хлорфенил)сульфонил]глицил}амино)метил]коричная кислота,
3-(3-{[(N-(3-хлор-2-метилфенил)-N-{[4-(трифторметил)фенил]сульфонил}глицил)амино]метил}фенил)пропионовая кислота,
3-[({N-(3-хлор-2-метилфенил)-N-[(2-фтор-4-метилфенил)сульфонил]глицил}амино)метил]бензойная кислота,
2-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]-1,3-оксазол-4-карбоновая кислота,
4-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]тиофен-2-карбоновая кислота,
(2S)-2-{3-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]фенокси}пропионовая кислота и
(2R)-2-{3-[({N-(3-хлор-2-метилфенил)-N-[(4-метилфенил)сульфонил]глицил}амино)метил]фенокси}пропионовая кислота.
11. Фармацевтическая композиция, содержащая в качестве активного ингредиента соединение или его фармацевтически приемлемую соль по п.3.
12. Фармацевтическая композиция по п.11, которая является антагонистом рецептора EP1.
13. Фармацевтическая композиция по п.11, которая является терапевтическим средством для лечения симптома нижних мочевыводящих путей.
14. Фармацевтическая композиция по п.13, причем заболеванием, приводящим к симптому нижних мочевыводящих путей, является гиперактивный мочевой пузырь, доброкачественная гиперплазия предстательной железы, контрактура шейки мочевого пузыря, цистит или простатит.
15. Применение соединения или его фармацевтически приемлемой соли по п.3 для получения средства для лечения симптома нижних мочевыводящих путей.
16. Применение по п.15, причем заболеванием, приводящим к симптому нижних мочевыводящих путей, является гиперактивный мочевой пузырь, доброкачественная гиперплазия предстательной железы, контрактура шейки мочевого пузыря, цистит или простатит.
17. Способ лечения симптома нижних мочевыводящих путей, включающий введение пациенту терапевтически эффективного количества соединения или его фармацевтически приемлемой соли по п.3.
18. Способ по п.17, причем заболеванием, приводящим к симптому нижних мочевыводящих путей, является гиперактивный мочевой пузырь, доброкачественная гиперплазия предстательной железы, контрактура шейки мочевого пузыря, цистит или простатит.
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