RU2007125692A - TETRAHYDROPYRIDIN-4-IL INDOLES WITH A COMBINATION OF PROPERTIES-RELATIONSHIPS FOR D2 DOPAMINE RECEPTORS D2 AND SEROTONIN REVERSION CENTERS - Google Patents

TETRAHYDROPYRIDIN-4-IL INDOLES WITH A COMBINATION OF PROPERTIES-RELATIONSHIPS FOR D2 DOPAMINE RECEPTORS D2 AND SEROTONIN REVERSION CENTERS Download PDF

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RU2007125692A
RU2007125692A RU2007125692/04A RU2007125692A RU2007125692A RU 2007125692 A RU2007125692 A RU 2007125692A RU 2007125692/04 A RU2007125692/04 A RU 2007125692/04A RU 2007125692 A RU2007125692 A RU 2007125692A RU 2007125692 A RU2007125692 A RU 2007125692A
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compound according
represents hydrogen
alkyl
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tautomers
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ХЕС Рулоф ВАН (NL)
ХЕС Рулоф ВАН
Питер СМИД (NL)
Питер Смид
Корнелис Г. Крюсе (NL)
Корнелис Г. Крюсе
Мартинус Т. М. ТЮЛП (NL)
Мартинус Т. М. ТЮЛП
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Солвей Фармасьютикалс Б.В. (Nl)
Солвей Фармасьютикалс Б.В.
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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
    • C07D401/14—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 three or more hetero rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • 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
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (10)

1. Производные тетрагидропиридин-4-ил индолов формулы (I)1. Derivatives of tetrahydropyridin-4-yl indoles of the formula (I)
Figure 00000001
Figure 00000001
 и их таутомеры, стереоизомеры, пролекарства, N-оксиды, фармакологичеки приемлемые соли, гидраты и сольваты,and their tautomers, stereoisomers, prodrugs, N-oxides, pharmacologically acceptable salts, hydrates and solvates, в которой R1 представляет собой водород, галоген, алкил (С1-3) или алкоксил (С1-3), CN или CF3,in which R 1 represents hydrogen, halogen, alkyl (C 1-3 ) or alkoxyl (C 1-3 ), CN or CF 3 , R2 представляет собой водород или алкил (С1-3),R 2 represents hydrogen or alkyl (C 1-3 ), R3 представляет собой водород или алкил (С1-3),R 3 represents hydrogen or alkyl (C 1-3 ), Z представляет собой водород или алкил (С1-3), алкоксил (С1-3) или алкилтиогруппу (С1-3),Z represents hydrogen or alkyl (C 1-3 ), alkoxyl (C 1-3 ) or alkylthio group (C 1-3 ), A представляет собой водород или алкил (С1-3), илиA represents hydrogen or alkyl (C 1-3 ), or A и Z вместе образуют насыщенный или ненасыщенный (частично) 5- или 6-членный цикл, который может быть замещен галогеном, алкилом (С1-3) или фенилом, причем Z в кольце представляет собой углерод, серу или азот.A and Z together form a saturated or unsaturated (partially) 5- or 6-membered ring, which may be substituted by halogen, alkyl (C 1-3 ) or phenyl, with Z in the ring being carbon, sulfur or nitrogen. 2. Соединение по п.1 и его таутомеры, стереоизомеры, пролекарства, N-оксиды, фармакологически приемлемые соли, гидраты и сольваты, в котором R1 представляет собой водород или галоген, R2 является водородом, R3 представляет собой CH3, Z представляет собой SCH3 и A представляет собой CH3 или Z+A образуют ненасыщенный (частично) 6-членный цикл, который может быть замещен CH3, C2H5 или изо-C3H7.2. The compound according to claim 1 and its tautomers, stereoisomers, prodrugs, N-oxides, pharmacologically acceptable salts, hydrates and solvates, in which R 1 represents hydrogen or halogen, R 2 represents hydrogen, R 3 represents CH 3 , Z represents SCH 3 and A represents CH 3 or Z + A form an unsaturated (partially) 6-membered ring which may be substituted with CH 3 , C 2 H 5 or iso- C 3 H 7 . 3. Соединение по п.1 и его таутомеры, стереоизомеры, пролекарства, N-оксиды, фармакологически приемлемые соли, гидраты и сольваты, в котором R1=R2=H, R3 является CH3 и Z+A вместе представляют -C(CH3)=CH-CH=CH-.3. The compound according to claim 1 and its tautomers, stereoisomers, prodrugs, N-oxides, pharmacologically acceptable salts, hydrates and solvates, in which R 1 = R 2 = H, R 3 is CH 3 and Z + A together represent -C (CH 3 ) = CH-CH = CH-. 4. Соединение по п.1, выбранное из группы4. The compound according to claim 1, selected from the group
Figure 00000002
Figure 00000002
 RR 1one RR 22 RR 33 ZZ AA (Z+A)(Z + A)
Z AZ a ZZ AA HH HH CH3 CH 3 -- -- -CH=CH-CH=CH--CH = CH-CH = CH- 7-CI7-ci HH CH3 CH 3 -- -- -CH=CH-CH=CH--CH = CH-CH = CH- 5-CH35-ch3 HH CH3 CH 3 -- -- -CH=CH-CH=CH--CH = CH-CH = CH- 6-CI6-ci HH CH3 CH 3 -- -- -CH=CH-CH=CH--CH = CH-CH = CH- 5-CI5-ci HH CH3 CH 3 -- -- -CH=CH-CH=CH--CH = CH-CH = CH- 5-CN5-cn HH CH3 CH 3 -- -- -CH=CH-CH=CH--CH = CH-CH = CH- 5-F5-f HH CH3 CH 3 -- -- -CH=CH-CH=CH--CH = CH-CH = CH- 5-Br5-br HH CH3 CH 3 -- -- -CH=CH-CH=CH--CH = CH-CH = CH- HH HH CH3 CH 3 -- -- -CH=CH-C(CH3)=CH--CH = CH-C (CH 3 ) = CH- HH HH CH3 CH 3 -- -- -S-CH2-CH2--S-CH 2 -CH 2 - HH HH CH3 CH 3 -- -- -S-CH=CH--S-CH = CH- HH HH CH3 CH 3 SCH3 SCH 3 CH3 CH 3 -- 7-CH3 7-CH 3 HH CH3 CH 3 -- -- -CH=CH-CH=CH--CH = CH-CH = CH- HH HH CH3 CH 3 SCH3 SCH 3 HH -- HH HH CH3 CH 3 -- -- -CH=C(CH3)-CH=CH--CH = C (CH 3 ) -CH = CH- HH HH CH3 CH 3 -- -- -S-CH=C(C6H6)--S-CH = C (C 6 H 6 ) - HH HH CH3 CH 3 -- -- -NH-(CH2)3--NH- (CH 2 ) 3 - HH HH CH3 CH 3 OCH3 Och 3 CH3 CH 3 -- 5-F5-f HH CH3 CH 3 SCH3 SCH 3 CH3 CH 3 -- HH CH3 CH 3 CH3 CH 3 SCH3 SCH 3 CH3 CH 3 -- 5-F5-f HH CH3 CH 3 -- -- -CH=C(CH3)-CH=CH--CH = C (CH 3 ) -CH = CH- HH HH CH3 CH 3 -- -- -C(CH3)=CH-CH=CH--C (CH 3 ) = CH-CH = CH- HH HH CH3 CH 3 -- -- -CH=CH-CH=C(CH3)--CH = CH-CH = C (CH 3 ) - 5-F5-f HH CH3 CH 3 -- -- -CH=C(C2H5)-CH=CH--CH = C (C 2 H 5 ) -CH = CH- HH HH CH3 CH 3 -- -- -CH=C(C2H5)-CH=CH--CH = C (C 2 H 5 ) -CH = CH- 5-F5-f HH CH3 CH 3 -- -- -C(CH3)=CH-CH=CH--C (CH 3 ) = CH-CH = CH- HH HH CH3 CH 3 -- -- -CH=C(C6H5)-CH=CH--CH = C (C 6 H 5 ) -CH = CH- 5-F5-f HH CH3 CH 3 -- -- -CH=C(i-C3H7)-CH=CH--CH = C (iC 3 H 7 ) -CH = CH- HH HH CH3 CH 3 -- -- -CH=C(i-C3H7)-CH=CH--CH = C (iC 3 H 7 ) -CH = CH- 5-CI5-ci HH C2H5 C 2 H 5 HH CH3 CH 3 -- 5-Br5-br HH C2H5 C 2 H 5 HH CH3 CH 3 -- 5-CN5-cn HH C2H5 C 2 H 5 HH CH3 CH 3 -- 5-F5-f HH CH3 CH 3 HH CH3 CH 3 --
и его таутомеры, стереоизомеры, пролекарства, N-оксиды, фармакологически приемлемые соли, гидраты и сольваты.and its tautomers, stereoisomers, prodrugs, N-oxides, pharmacologically acceptable salts, hydrates and solvates. 5. Способ получения соединений по п.1, отличающийся тем, что соединение формулы (II)5. The method of producing compounds according to claim 1, characterized in that the compound of formula (II)
Figure 00000003
Figure 00000003
 вступает в реакцию в оснóвной среде с соединением формулы (III)reacts in the basic medium with a compound of formula (III)
Figure 00000004
Figure 00000004
 в которой символы имеют те же значения, что в п.1, и L представляет собой так называемую уходящую группу.in which the symbols have the same meanings as in claim 1, and L represents the so-called leaving group. 6. Фармацевтическая композиция, включающая кроме фармацевтически приемлемого носителя и/или по меньшей мере одного фармацевтически приемлемого вспомогательного вещества фармакологически активное количество по меньшей мере одного соединения по п.1 или его соли в качестве активного ингредиента.6. A pharmaceutical composition comprising, in addition to a pharmaceutically acceptable carrier and / or at least one pharmaceutically acceptable excipient, a pharmacologically active amount of at least one compound according to claim 1 or a salt thereof as an active ingredient. 7. Способ получения композиции по п.6, отличающийся тем, что соединение по п.1 переводят в форму, пригодной для введения.7. The method of obtaining the composition according to claim 6, characterized in that the compound according to claim 1 is converted into a form suitable for administration. 8. Соединение по любому из пп.1-4 или его соль для применения в качестве медикамента.8. The compound according to any one of claims 1 to 4 or its salt for use as a medicine. 9. Применение соединения по любому из пп.1-4 для приготовления фармацевтической композиции для лечения заболеваний ЦНС.9. The use of a compound according to any one of claims 1 to 4 for the preparation of a pharmaceutical composition for the treatment of central nervous system diseases. 10. Применение по п.9, отличающееся тем, что указанные заболевания ЦНС включают агрессию, беспокойство, аутизм, головокружение, нарушения обучаемости или памяти, шизофрению и другие психотические заболевания. 10. The use according to claim 9, characterized in that the said diseases of the central nervous system include aggression, anxiety, autism, dizziness, impaired learning or memory, schizophrenia and other psychotic diseases.
RU2007125692/04A 2004-12-07 2005-12-06 TETRAHYDROPYRIDIN-4-IL INDOLES WITH A COMBINATION OF PROPERTIES-RELATIONSHIPS FOR D2 DOPAMINE RECEPTORS D2 AND SEROTONIN REVERSION CENTERS RU2007125692A (en)

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US63343904P 2004-12-07 2004-12-07
EP04106351.2 2004-12-07
EP04106351 2004-12-07
US60/633,439 2004-12-07

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EP (1) EP1828168A2 (en)
JP (1) JP2008523027A (en)
KR (1) KR20070091009A (en)
CN (1) CN101072770A (en)
AR (1) AR052146A1 (en)
AU (1) AU2005313387A1 (en)
BR (1) BRPI0518465A2 (en)
CA (1) CA2587936A1 (en)
MX (1) MX2007006757A (en)
RU (1) RU2007125692A (en)
SA (1) SA05260388B1 (en)
TW (1) TW200626575A (en)
WO (1) WO2006061373A2 (en)
ZA (1) ZA200704155B (en)

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BRPI0905938A2 (en) * 2008-02-05 2018-05-29 Watson Pharma Private Ltd process for preparing 3- (2-chloroethyl) -2-methylhydroxy-4h-pyrido [1,2-a] pyrimidine-4-one of 3- (2-chloroethyl) -6,7,8,9-tetrahydro 3- [2- [4- (6-Fluoro-1,2-benzisoxazol-3-yl) -1-9-hydroxy-2-methyl-4h-pyrido [1,2-a] pyrimidin-4-one crude -piperidinyl] ethyl] -6,7,8,9-thetahydro-9-hydroxy-2-methyl-4h-pyrido [1,2-a] pyrimidine-4-one, and process for purifying paliperidone

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GB8900382D0 (en) * 1989-01-09 1989-03-08 Janssen Pharmaceutica Nv 2-aminopyrimidinone derivatives
CA2373855A1 (en) * 1999-05-12 2000-11-23 Solvay Pharmaceuticals B.V. Method of treating psychotic disorders
AU2003257407A1 (en) * 2002-08-29 2004-03-19 H. Lundbeck A/S S-(+)-3-{1-(2-(2,3-dihydro-1h-indol-3-yl)ethyl)-3,6-dihydro-2h-pyridin-4-yl}-6-chloro-1h-indole and acid addition salts thereof

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BRPI0518465A2 (en) 2008-11-18
CN101072770A (en) 2007-11-14
EP1828168A2 (en) 2007-09-05
WO2006061373A3 (en) 2006-09-21
JP2008523027A (en) 2008-07-03
ZA200704155B (en) 2008-08-27
CA2587936A1 (en) 2006-06-15
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