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RU2007111123A - Производные арилсульфонилстильбена для лечения бессоницы и связанных с ней расстройств - Google Patents

Производные арилсульфонилстильбена для лечения бессоницы и связанных с ней расстройств Download PDF

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Publication number
RU2007111123A
RU2007111123A RU2007111123/04A RU2007111123A RU2007111123A RU 2007111123 A RU2007111123 A RU 2007111123A RU 2007111123/04 A RU2007111123/04 A RU 2007111123/04A RU 2007111123 A RU2007111123 A RU 2007111123A RU 2007111123 A RU2007111123 A RU 2007111123A
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Russia
Prior art keywords
phenyl
sulfonyl
vinyl
fluorophenyl
compound
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RU2007111123/04A
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RU2382766C2 (ru
Inventor
Мира ДЖИЛЛИГАН (GB)
Мира ДЖИЛЛИГАН
Александр Чарльз ХАМФРИЗ (GB)
Александр Чарльз ХАМФРИЗ
Питер Алан ХАНТ (GB)
Питер Алан ХАНТ
Тамара ЛАДДУВАХЕТТИ (GB)
Тамара Ладдувахетти
Ангус Мюррей МАКЛЕОД (GB)
Ангус Мюррей МАКЛЕОД
Кевин Джон МЕРЧАНТ (GB)
Кевин Джон Мерчант
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Мерк Шарп энд Домэ Лимитед (GB)
Мерк Шарп Энд Домэ Лимитед
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    • C—CHEMISTRY; METALLURGY
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    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
    • A61K31/10—Sulfides; Sulfoxides; Sulfones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 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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    • C07D211/06—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
    • C07D211/36—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 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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    • C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring

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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Claims (11)

1. Соединение формулы I
Figure 00000001
или его фармацевтически приемлемые соль или гидрат, где
n является 0 или 1;
R1 обозначает H или F;
R2 обозначает галоген, CN, CONH2, C1-4алкил или C1-4алкокси;
R7 обозначает H или C1-4алкил; и
и Z обозначает гидроксиC1-6алкил или C1-6алкоксикарбонил,
или 5- или 6-членное гетероароматическое
кольцо, которое необязательно имеет метильную замещающую группу.
2. Соединение по п. 1, в котором Z обозначает гидроксиC1-6алкил.
3. Соединение по п. 1, в котором Z обозначает C1-6алкоксикарбонил.
4. Соединение по п. 1, в котором Z обозначает 5- или 6-членное гетероароматическое кольцо, которое необязательно имеет метильную замещающую группу.
5. Соединение по любому из предшествующих пунктов, в котором Z находится в орто-положении по отношению к сульфоновому компоненту в формуле I.
6. Соединение по п. 1, выбранное из
(1S)-l-[2-({4-[(E)-2-(4-фторфенил)винил]фенил}сульфонил)фенил]этанола;
(1S)-l-[2-({4-[(E)-2-(2,4-дифторфенил)винил]фенил}сульфонил)фенил]этанола;
(1S)-l-[2-({4-[(E)-2-(4-фторфенил)винил]-3-метилфенил}сульфонил)фенил]этанола;
[2-({4-[(E)-2-(4-фторфенил)винил]фенил}сульфонил)фенил]метанола;
[2-({4-[(E)-2-(2,4-дифторфенил)винил]фенил} сульфонил)фенил]метанола;
2-[2-({4-[(E)-2-(4-фторфенил)винил]фенил}сульфонил)фенил]пропан-2-ола;
2-[2-({4-[(E)-2-(2,4-дифторфенил)винил]фенил}сульфонил)фенил]пропан-2-ола;
2-[2-({4-[(E)-2-(4-фторфенил)винил]фенил}сульфонил)фенил]этанола;
метил-2-({4-[(Ε)-2-(2,4-дифторфенил)винил]фенил}сульфонил)бензоата;
метил-2-({4-[(E)-2-(4-фторфенил)винил]фенил}сульфонил)бензоата;
метил 3-({4-[(E)-2-(4-фторфенил)винил]фенил}сульфонил)бензоата;
метил-2-({4-[(E)-2-(4-фторфенил)винил]фенил}сульфонил)-3-метилбензоата;
2-[2-({4-[(E)-2-(2,4-дифторфенил)винил]фенил}сульфонил)фенил]-lH-имидазола;
2-[2-({4-[(E)-2-(4-фторфенил)винил]фенил}сульфонил)фенил]-lH-имидазола;
2-[2-({4-[(E)-2-(2,4-дифторфенил)винил]фенил}сульфонил)фенил]-l,3,4-оксадиазола;
и
2-[2-({4-[(E)-2-(4-фторфенил)винил]фенил}сульфонил)фенил]-l,3,4-оксадиазола;
и его фармацевтически приемлемые соли или гидраты.
7. Фармацевтическая композиция, содержащая соединение по любому из предшествующих пунктов и фармацевтически приемлемый носитель.
8. Применение соединения по любому из пп. 1-6 для изготовления лекарственного средства для лечения нарушения, обусловленного активностью рецептора 5-HT2A.
9. Фармацевтическая композиция по п. 7, которая дополнительно содержит габоксадол.
10. Комбинация соединения по любому из пп. 1-6 и габоксадола для применения в лечении или предотвращении расстройств сна, шизофрении или депрессии.
11. Способ получения соединения формулы I по п. 1, включающий реакцию производного бром- или иодбензола (9) с солью стильбенсульфиновой кислоты (10):
Figure 00000002
где X2 обозначает Br или I, а R1, R2, R7, n и Z определены в п. 1.
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