RU2011108024A - 3-азабицикло(3.1.0) гексильные производные в качестве модуляторов метаботропных глутаматных рецепторов - Google Patents
3-азабицикло(3.1.0) гексильные производные в качестве модуляторов метаботропных глутаматных рецепторов Download PDFInfo
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- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims 2
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims 2
- CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical class [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- -1 cyano, hydroxyl Chemical group 0.000 claims abstract 14
- 125000005843 halogen group Chemical group 0.000 claims abstract 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 239000012453 solvate Substances 0.000 claims abstract 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 4
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims abstract 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 3
- 230000002265 prevention Effects 0.000 claims 6
- 208000012902 Nervous system disease Diseases 0.000 claims 5
- 208000028017 Psychotic disease Diseases 0.000 claims 5
- 208000015114 central nervous system disease Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000019022 Mood disease Diseases 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 230000003281 allosteric effect Effects 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 230000003227 neuromodulating effect Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000008811 Agoraphobia Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000020186 Schizophreniform disease Diseases 0.000 claims 1
- 206010041250 Social phobia Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 208000026725 cyclothymic disease Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000024732 dysthymic disease Diseases 0.000 claims 1
- 208000029364 generalized anxiety disease Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 208000024714 major depressive disease Diseases 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 1
- 208000022821 personality disease Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000019899 phobic disease Diseases 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 0 CC(C(N(*)C=C1)=O)=C1N(C1)CC2C1C2*[Al] Chemical compound CC(C(N(*)C=C1)=O)=C1N(C1)CC2C1C2*[Al] 0.000 description 1
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- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
1. Соединение, имеющее формулу (I) ! , ! или его стереохимически изомерная форма, где ! R1 представляет собой С1-6алкил или С1-3алкил, замещенный С3-7циклоалкилом, галогено, фенилом или фенилом, замещенным галогено, трифторметилом или трифторметокси; !R2 представляет собой галогено, трифторметил, С1-3алкил или циклопропил; ! Х представляет собой ковалентную связь, О, NR3, NR3-CH2 или О-СН2; ! R3 представляет собой водород или С1-3алкил; и ! Ar представляет собой незамещенный фенил или фенил, замещенный n радикалами R4, ! где n равен 1, 2 или 3; ! где каждый R4 независимо выбран из группы, состоящей из галогено, С1-3алкила, гидроксиС1-3алкила, полигалогеноС1-3алкила, циано, гидроксила, амино, карбоксила, С1-3алкилоксиС1-3алкила, С1-3алкилокси, полигалогеноС1-3алкилокси, С1-3алкилкарбонила, моно- и ди(С1-3алкил)амино и морфолинила; ! или где два соседних радикала R4, взятые вместе, образуют бивалентный радикал формулы ! -N=CH-NH- (а), или ! -СН=СН-NH- (b), или ! -O-CH2-CH2-NH- (с); или ! его фармацевтически приемлемые соль присоединения или сольват. ! 2. Соединение по п.1 или его стереохимически изомерная форма, где ! R1 представляет собой С1-6алкил или C1-3алкил, замещенный С3-7циклоалкилом, фенилом или фенилом, замещенным галогено, трифторметилом или трифторметокси; ! R2 представляет собой галогено, трифторметил, C1-3алкил или циклопропил; ! Х представляет собой ковалентную связь, О, NR3, NR3-CH2 или O-CH2; ! R3 представляет собой водород или C1-3алкил; и ! Ar представляет собой незамещенный фенил или фенил, замещенный n радикалами R4, ! где n равен 1, 2 или 3; ! где каждый R4 независимо выбран из группы, состоящей из галогено, C1-3алкила, гидроксиС1-3алкила, полигалогеноС1-3алкила, циано, гидроксила, амино, к�
Claims (16)
1. Соединение, имеющее формулу (I)
или его стереохимически изомерная форма, где
R1 представляет собой С1-6алкил или С1-3алкил, замещенный С3-7циклоалкилом, галогено, фенилом или фенилом, замещенным галогено, трифторметилом или трифторметокси;
R2 представляет собой галогено, трифторметил, С1-3алкил или циклопропил;
Х представляет собой ковалентную связь, О, NR3, NR3-CH2 или О-СН2;
R3 представляет собой водород или С1-3алкил; и
Ar представляет собой незамещенный фенил или фенил, замещенный n радикалами R4,
где n равен 1, 2 или 3;
где каждый R4 независимо выбран из группы, состоящей из галогено, С1-3алкила, гидроксиС1-3алкила, полигалогеноС1-3алкила, циано, гидроксила, амино, карбоксила, С1-3алкилоксиС1-3алкила, С1-3алкилокси, полигалогеноС1-3алкилокси, С1-3алкилкарбонила, моно- и ди(С1-3алкил)амино и морфолинила;
или где два соседних радикала R4, взятые вместе, образуют бивалентный радикал формулы
-N=CH-NH- (а), или
-СН=СН-NH- (b), или
-O-CH2-CH2-NH- (с); или
его фармацевтически приемлемые соль присоединения или сольват.
2. Соединение по п.1 или его стереохимически изомерная форма, где
R1 представляет собой С1-6алкил или C1-3алкил, замещенный С3-7циклоалкилом, фенилом или фенилом, замещенным галогено, трифторметилом или трифторметокси;
R2 представляет собой галогено, трифторметил, C1-3алкил или циклопропил;
Х представляет собой ковалентную связь, О, NR3, NR3-CH2 или O-CH2;
R3 представляет собой водород или C1-3алкил; и
Ar представляет собой незамещенный фенил или фенил, замещенный n радикалами R4,
где n равен 1, 2 или 3;
где каждый R4 независимо выбран из группы, состоящей из галогено, C1-3алкила, гидроксиС1-3алкила, полигалогеноС1-3алкила, циано, гидроксила, амино, карбоксила, С1-3алкилоксиС1-3алкила, C1-3алкилокси, полигалогеноС1-3алкилокси, C1-3алкилкарбонила, моно- и ди(С1-3алкил)амино и морфолинила;
или где два соседних радикала R4, взятые вместе, образуют бивалентный радикал формулы
-N=CH-NH- (а), или
-CH=CH-NH- (b), или
-O-CH2-CH2-NH- (с); или
его фармацевтически приемлемые соль присоединения или сольват.
3. Соединение по п.1 или его стереохимически изомерная форма, где
R1 представляет собой 1-бутил, 2-метил-1-пропил, 3-метил-1-бутил, (циклопропил)метил или 2-(циклопропил)-1-этил;
R2 представляет собой хлоро;
Х представляет собой ковалентную связь или О-СН2; и
Ar представляет собой незамещенный фенил или фенил, замещенный n радикалами R4,
где n равен 1, 2 или 3;
где каждый R4 независимо выбран из группы, состоящей из галогено, трифторметила, морфолинила или гидроксиС1-3алкила;
или его фармацевтически приемлемые соль присоединения или сольват.
4. Соединение по п.1 или его стереохимически изомерная форма, где
R1 представляет собой 1-бутил, 2-метил-1-пропил, 3-метил-1-бутил, (циклопропил)метил или 2-(циклопропил)-1-этил;
R2 представляет собой хлоро;
Х представляет собой ковалентную связь или O-СН2; и
Ar представляет собой незамещенный фенил или фенил, замещенный n радикалами R4,
где n равен 2;
где каждый R4 независимо выбран из группы, состоящей из галогено;
или его фармацевтически приемлемые соль присоединения или сольват.
5. Соединение по п.1 или его стереохимически изомерная форма, где
R1 представляет собой 1-бутил, 3-метил-1-бутил, (циклопропил)метил или 2-(циклопропил)-1-этил;
R2 представляет собой хлоро;
Х представляет собой ковалентную связь или O-СН2; и
Ar представляет собой незамещенный фенил или 2,5-дихлорфенил;
или его фармацевтически приемлемые соль присоединения или сольват.
6. Соединение по п.1, выбранное из:
(2аα,3β,3аα)-1-бутил-3-хлор-4-[6-[(2,5-дихлор-феноксиметил)-3-аза-бицикло[3.1.0]гекс-3-ил]-1H-пиридин-2-она;
(2аα,3α,3аα)-1-бутил-3-хлор-4-[6-[(2,5-дихлор-феноксиметил)-3-аза-бицикло[3.1.0]гекс-3-ил]-1H-пиридин-2-она;
(2аα,3α,3аα)-1-бутил-3-хлор-4-(6-фенил-3-аза-бицикло[3.1.0]гекс-3-ил)-1H-пиридин-2-она;
(2аα,3α,3аα)-3-хлор-1-циклопропилметил-4-(6-фенил-3-аза-бицикло[3.1.0]гекс-3-ил)-1H-пиридин-2-она;
или его фармацевтически приемлемые соль присоединения или сольват.
7. Фармацевтическая композиция, содержащая терапевтически эффективное количество соединения по любому из пп.1-6 и фармацевтически приемлемый носитель или эксципиент.
8. Соединение по любому из пп.1-6 для применения в качестве лекарственного средства.
9. Применение соединения по любому из пп.1-6 или фармацевтической композиции по п.7 для изготовления лекарственного средства для лечения или предупреждения состояния у млекопитающего, включая человека, на лечение или предупреждение которого влияет нейромодуляторный эффект положительных аллостерических модуляторов метаботропного глутаматного рецептора 2 подтипа (mGluR2), или лечению или предупреждению которого он способствует.
10. Применение соединения по любому из пп.1-6 или фармацевтической композиции по п.7 для изготовления лекарственного средства для лечения или предупреждения расстройства центральной нервной системы, выбранного из группы, состоящей из тревожных расстройств, психотических расстройств, расстройств личности, расстройств, вызванных приемом психоактивных веществ, расстройств пищевого поведения, расстройств настроения, мигрени, эпилепсии или судорожных расстройств, расстройств детского возраста, когнитивных расстройств, нейродегенерации, нейротоксичности и ишемии.
11. Применение по п.10, где расстройство центральной нервной системы представляет собой тревожное расстройство, выбранное из группы, состоящей из агорафобии, генерализованного тревожного расстройства, обсессивно-компульсивного расстройства, панического расстройства, посттравматического стрессового расстройства, социальной фобии и других фобий.
12. Применение по п.10, где расстройство центральной нервной системы представляет собой психотическое расстройство, выбранное из группы, состоящей из шизофрении, бредового расстройства, шизоаффективного расстройства, шизофреноформного расстройства и психотического расстройства, вызванного приемом психоактивных веществ.
13. Применение по п.10, где расстройство центральной нервной системы представляет собой расстройство настроения, выбранное из группы, состоящей из биполярных расстройств (I и II типа), циклотимического расстройства, депрессии, дистимического расстройства, большого депрессивного расстройства и расстройства настроения, вызванного приемом психоактивных веществ.
14. Применение по п.10, где расстройство центральной нервной системы выбрано из группы, состоящей из тревоги, шизофрении, мигрени, депрессии и эпилепсии.
15. Применение соединения по любому из пп.1-6 в комбинации с ортостерическим агонистом mGluR2 для изготовления лекарственного средства для лечения или предупреждения состояния, охарактеризованного в любом из пп.9-14.
16. Продукт, содержащий
а) соединение по любому из пп.1-6; и
б) ортостерический агонист mGluR2,
в качестве комбинированного препарата для одновременного, раздельного или последовательного применения в лечении или предупреждении состояния у млекопитающего, на лечение или предупреждение которого влияет нейромодуляторный эффект аллостерических модуляторов mGluR2, или лечению или предупреждению которого он способствует.
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| PCT/EP2009/006326 WO2010025890A1 (en) | 2008-09-02 | 2009-09-01 | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
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-
2009
- 2009-09-01 JP JP2011525455A patent/JP5547194B2/ja not_active Expired - Fee Related
- 2009-09-01 ES ES09778252.8T patent/ES2439291T3/es active Active
- 2009-09-01 US US13/061,183 patent/US8691849B2/en not_active Expired - Fee Related
- 2009-09-01 MX MX2011002042A patent/MX2011002042A/es active IP Right Grant
- 2009-09-01 CN CN200980134293XA patent/CN102143955B/zh not_active Expired - Fee Related
- 2009-09-01 RU RU2011108024/04A patent/RU2510396C2/ru not_active IP Right Cessation
- 2009-09-01 EP EP09778252.8A patent/EP2344470B1/en active Active
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- 2009-09-01 CA CA2735764A patent/CA2735764C/en not_active Expired - Fee Related
- 2009-09-01 AU AU2009289784A patent/AU2009289784B2/en not_active Ceased
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| MX2011002042A (es) | 2011-06-20 |
| EP2344470A1 (en) | 2011-07-20 |
| EP2344470B1 (en) | 2013-11-06 |
| US8691849B2 (en) | 2014-04-08 |
| CN102143955B (zh) | 2013-08-14 |
| CN102143955A (zh) | 2011-08-03 |
| JP2012501352A (ja) | 2012-01-19 |
| RU2510396C2 (ru) | 2014-03-27 |
| JP5547194B2 (ja) | 2014-07-09 |
| CA2735764C (en) | 2016-06-14 |
| AU2009289784A1 (en) | 2010-03-11 |
| CA2735764A1 (en) | 2010-03-11 |
| WO2010025890A1 (en) | 2010-03-11 |
| ES2439291T3 (es) | 2014-01-22 |
| US20110306642A1 (en) | 2011-12-15 |
| BRPI0918055A2 (pt) | 2015-12-01 |
| AU2009289784B2 (en) | 2012-03-22 |
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