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RU2004107218A - COMPOUNDS WITH ACTIVITY AGAINST MUSCARINE RECEPTORS AND A MEDICINE ON ITS BASIS - Google Patents

COMPOUNDS WITH ACTIVITY AGAINST MUSCARINE RECEPTORS AND A MEDICINE ON ITS BASIS Download PDF

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RU2004107218A
RU2004107218A RU2004107218/04A RU2004107218A RU2004107218A RU 2004107218 A RU2004107218 A RU 2004107218A RU 2004107218/04 A RU2004107218/04 A RU 2004107218/04A RU 2004107218 A RU2004107218 A RU 2004107218A RU 2004107218 A RU2004107218 A RU 2004107218A
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alkyl
disease
aryl
condition
cycloalkyl
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RU2278111C2 (en
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Марк Роберт БРЭНН (US)
Марк Роберт БРЭНН
Терри МЕССИЕР (US)
Терри МЕССИЕР
Эрика Энн КАРРИЕР (US)
Эрика Энн КАРРИЕР
Катаран Лаури ДАДЖЕНТО (US)
Катаран Лаури ДАДЖЕНТО
Микаэль ФРИБЕРГ (SE)
Микаэль ФРИБЕРГ
Нильс СКЬЕРБЕК (DK)
Нильс СКЬЕРБЕК
Трэйси СПЭЛДИНГ (US)
Трэйси СПЭЛДИНГ
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Акадиа Фармасьютикалз, Инк. (Us)
Акадиа Фармасьютикалз, Инк.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—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
    • 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
    • C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • 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
    • C07D211/08—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
    • C07D211/18—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
    • C07D211/20—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
    • C07D211/22—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 oxygen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/60—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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/60—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
    • C07D213/62—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
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  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (6)

1. Соединение формулы I для использования в лечении человека или животного путем применения на практике терапии на человеке или животном1. The compound of formula I for use in the treatment of a human or animal by practical application of therapy on a human or animal
Figure 00000001
Figure 00000001
 где Х1, Х2, Х3, Х4 и Х5 выбираются из СН2, NH и О;where X 1 , X 2 , X 3 , X 4 and X 5 are selected from CH 2 , NH and O; k равно 0 или 1;k is 0 or 1; R1 является нормальным или разветвленным С1-8 алкилом, С2-8 алкенилом, С2-8 алкинилом, С1-8 алкилиденом, С1-8 алкокси, С1-8 гетероалкилом, С1-8 аминоалкилом, С1-8 галогеналкилом, С1-8 алкоксикарбонилом, С1-8 гидроксиалкокси, С1-8 гидроксиалкилом, -SH, С1-8 алкилтио, -О-СН2-С5-6 арилом, -С(О)-С5-6 арилом, замещенным С1-3 алкилом или галогеном; С5-6 арилом или С5-6 циклоалкилом, необязательно включающими 1 или более гетероатомов, выбранных из N, S и О; -С(О)NR3R4, -NR3R4, -NR3C(O)NR4R5, -CR3R4, -OC(O)R3, -(O)(CH2)sNR3R4 или -(CH2)sNR3R4, где R3, R4 и R5 являются одинаковыми или разными, каждый независимо выбирается из Н, С1-6 алкила; С5-6 арила, необязательно включающего 1 или более гетероатомов, выбранных из N, O и S, и необязательно замещенного галогеном или С1-6 алкилом; С3-6 циклоалкила, или R3 и R4 вместе с атомом N, когда они присутствуют, образуют циклическую кольцевую структуру, включающую 5-6 атомов, выбранных из C, N, S и О; и s равно целому числу от 0 до 8;R 1 is straight or branched C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 1-8 alkylidene, C 1-8 alkoxy, C 1-8 heteroalkyl, C 1-8 aminoalkyl, C 1 -8 haloalkyl, C 1-8 alkoxycarbonyl, C 1-8 hydroxyalkoxy, C 1-8 hydroxyalkyl, -SH, C 1-8 alkylthio, -O-CH 2 -C 5-6 aryl, -C (O) -C 5-6 aryl substituted with C 1-3 alkyl or halogen; With 5-6 aryl or C 5-6 cycloalkyl, optionally including 1 or more heteroatoms selected from N, S and O; -C (O) NR 3 R 4 , -NR 3 R 4 , -NR 3 C (O) NR 4 R 5 , -CR 3 R 4 , -OC (O) R 3 , - (O) (CH 2 ) s NR 3 R 4 or - (CH 2 ) s NR 3 R 4 , where R 3 , R 4 and R 5 are the same or different, each independently selected from H, C 1-6 alkyl; C 5-6 aryl, optionally including 1 or more heteroatoms selected from N, O and S, and optionally substituted with halogen or C 1-6 alkyl; C 3-6 cycloalkyl, or R 3 and R 4, together with the N atom, when present, form a cyclic ring structure comprising 5-6 atoms selected from C, N, S and O; and s is an integer from 0 to 8; t равно 0, 1 или 2, радикалы R1, когда t равно 2, являются одинаковыми или разными;t is 0, 1 or 2, the radicals R 1 when t is 2 are the same or different; А является С5-12 арилом или С5-7 циклоалкилом, каждый необязательно включающий 1 или более гетероатомов, выбранных из N, S и О;A is C 5-12 aryl or C 5-7 cycloalkyl, each optionally including 1 or more heteroatoms selected from N, S and O; R2 является Н, амино, гидроксилом, галогеном или нормальным или разветвленным С1-6 алкилом, С2-6 алкенилом, С2-6 алкинилом, С1-6 алкокси, С1-6 гетероалкилом, С1-6 аминоалкилом, С1-6 галогеналкилом, С1-6 алкоксикарбонилом, С1-6 алкилтио, -CN, -CF3, -OR3, -COR3, NO2, -NHR3, -NHC(O)R3, -C(O)NR3R4, -NR3R4, -NR3C(O)NR4R5, -OC(O)R3, -C(O)R3R4, -O(CH2)qNR3, -CNR3R4 или -(CH2)qNR3R4, где q равно целому числу от 1 до 6;R 2 is H, amino, hydroxyl, halogen, or straight or branched C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 heteroalkyl, C 1-6 aminoalkyl, C 1-6 haloalkyl, C 1-6 alkoxycarbonyl, C 1-6 alkylthio, —CN, —CF 3 , —OR 3 , —COR 3 , NO 2 , —NHR 3 , —NHC (O) R 3 , —C (O) NR 3 R 4 , -NR 3 R 4 , -NR 3 C (O) NR 4 R 5 , -OC (O) R 3 , -C (O) R 3 R 4 , -O (CH 2 ) q NR 3 , —CNR 3 R 4, or - (CH 2 ) q NR 3 R 4 , where q is an integer from 1 to 6; n равно 0, 1, 2, 3 или 4, радикалы R2, где n > 1, являются одинаковыми или разными;n is 0, 1, 2, 3 or 4, the radicals R 2 , where n> 1, are the same or different; р равно 0 или целому числу от 1 до 5;p is 0 or an integer from 1 to 5; Y является O, S, CHOH, -NHC(O)-, -C(O)NH-, -C(O)-, -OC(O)-, NR7 или -CH=N-, и R7 является Н или С1-4 алкилом; или отсутствует;Y is O, S, CHOH, —NHC (O) -, —C (O) NH—, —C (O) -, —OC (O) -, NR 7 or —CH = N—, and R 7 is H or C 1-4 alkyl; or absent; Z является CR8R9, где R8 и R9 независимо выбираются из Н и нормального или разветвленного С1-8 алкила, его фармацевтически приемлемая соль, эфир или пролекарство.Z is CR 8 R 9 , where R 8 and R 9 are independently selected from H and straight or branched C 1-8 alkyl, a pharmaceutically acceptable salt, ester or prodrug thereof. 2. Лекарственный препарат для лечения заболеваний и состояний, связанных с агонистической активностью мускариновых рецепторов, включающий эффективное количество соединения (I) по п.1 или его фармацетически приемлемую соль, эфир или пролекарство и фармацевтически приемлемый носитель.2. A medicament for treating diseases and conditions associated with agonistic activity of muscarinic receptors, comprising an effective amount of compound (I) according to claim 1 or a pharmaceutically acceptable salt, ester or prodrug thereof, and a pharmaceutically acceptable carrier. 3. Лекарственный препарат по п.2, где заболеванием или состоянием является заболевание или состояние, связанное с пониженными уровнями ацетилхолина.3. The drug of claim 2, wherein the disease or condition is a disease or condition associated with lowered levels of acetylcholine. 4. Лекарственный препарат по п.3, где указанное заболевание или состояние является нейродегенеративным заболеванием, нарушением познавательной функции, возрастным снижением познавательной функции или слабоумием.4. The drug according to claim 3, where the specified disease or condition is a neurodegenerative disease, impaired cognitive function, age-related decrease in cognitive function or dementia. 5. Лекарственный препарат по п.2, где заболеванием или состоянием является заболевание или состояние, связанное с повышенным внутриглазным давлением.5. The drug according to claim 2, where the disease or condition is a disease or condition associated with increased intraocular pressure. 6. Лекарственный препарат по п.5, где указанное заболевание является глаукомой.6. The drug according to claim 5, where the specified disease is glaucoma.
RU2004107218/04A 1998-03-31 2004-03-11 Derivatives of nitrogen-containing heterocyclic compounds and medicinal agents based on thereof RU2278111C2 (en)

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