RU2003129638A - Новые соединения - Google Patents
Новые соединения Download PDFInfo
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- RU2003129638A RU2003129638A RU2003129638/04A RU2003129638A RU2003129638A RU 2003129638 A RU2003129638 A RU 2003129638A RU 2003129638/04 A RU2003129638/04 A RU 2003129638/04A RU 2003129638 A RU2003129638 A RU 2003129638A RU 2003129638 A RU2003129638 A RU 2003129638A
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- Prior art keywords
- alkyl
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- methyl
- heteroaryl
- alkenyl
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- 150000001875 compounds Chemical class 0.000 title claims 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 29
- -1 cyano, acetoxymethyl Chemical group 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 125000006224 2-tetrahydrofuranylmethyl group Chemical group [H]C([H])(*)C1([H])OC([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Chemical group 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- 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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- C07D403/12—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 chain containing hetero atoms as chain links
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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Claims (10)
1. Соединение формулы I или его фармацевтически приемлемая соль
где R1 выбран из группы, состоящей из -(С1-С8)алкила, -(С2-С8)алкенила, R N(C1-C6)алкила-, R NC(=0)(C1-C6)алкила-, R4O(С1-C6)алкила-, R4OC(=O)(C1-C6)алкила-, R4C(=O)(C1-C6)алкила-, R4C(=O)NR4(C1-C6)алкила-, R NSO2(C1-C6)алкила-, R4CSO2NR4(C1-C6)алкила-, R NC(=O)NR4(C1-C6)алкила-, R NSO2NR4(C1-C6)алкила-, радикалов арил(С1-С6)алкил, ароил(С1-С6)алкил, гетероарил(С1-С6)алкил, гетероароил(С1-С6)алкил, (С3-С8)гетероциклоалкил(С1-С6)алкил, бициклический гетероарил(С1-С6)алкил и бициклический гетероароил(С1-С6)алкил;
группировки R1 включают в себя незамещенный -(С2-С8)алкенил и -(C1-С8)алкил, незамещенный или замещенный одной или более чем одной группировкой, независимо выбранной из группы, состоящей из галогена, циано, ацетоксиметила и нитро;
Ar представляет собой возможно замещенную арильную группировку;
R2 представляет собой -(С1-С6)алкил, незамещенный или замещенный по 1-6 атомам углерода одним или более чем одним заместителем фтором, или (С3-С6)циклоалкил;
R3 выбран из группы, состоящей из
R4 представляет собой группировку, независимо выбранную из группы, состоящей из -Н, -(C1-С6)алкила, -(С2-С6)алкенила и -(С2-С6)алкинила,
группировки R5 независимо выбраны из группы, состоящей из -Н, -(С1-С6)алкила, -(С2-С6)алкенила и гетероциклила,
группировки R6 независимо выбраны из группы, состоящей из: -Н, -(C1-С6)алкила, -(С2-С6)алкенила и -(С1-С6)алканоила, гетероциклила, радикала гетероциклил(С1-С3)алкил, арила, радикала арил(С1-С3)алкил, гетероарила, радикалов гетероарил(С1-С3)алкил, бициклический гетероарил и бициклический гетероарил(С1-С3)алкил;
R5 и R6 могут объединяться с образованием 5-7-членного гетероцикла;
Х выбран из группы, состоящей из –C(R5)2-, -NR5-, C(=O)-, -CH2-CH2-, -СН=СН-, -О-, -C(R)(R’)- и -S(O)n- (где n равно 0, 1 или 2), где R и R’ представляют собой (С1-С6)алкил, OR” или Н, и R” представляет собой Н или (C1-С6)алкил; и
Y представляет собой углерод или азот,
где, если R1 представляет собой R N(C1-C6)алкил-, где оба R4 представляют собой -(С1-С6)алкил, то R3 не представляет собой ацетил, -NH2 или ацетамидо.
2. Соединение по п.1, где
R1 выбран из группы, состоящей из -(С1-С8)алкила, -(С2-С8)алкенила, радикала арил(С1-С6)алкил, R N(C1-C6)алкила-, R4O(C1-C6)алкила-, радикалов -гетероциклоалкил(С1-С6)алкил (где гетероциклил представляет собой 4-8-членное кольцо, включающее в себя один или более чем один гетероатом, выбранный из азота и кислорода) и гетероарил(С1-С6)алкил;
где арильные и гетероарильные группировки R1 являются незамещенными или замещены -(С1-С6)алкилом или галогеном;
R2 выбран из группы, состоящей из –СН3, -СН2СН3, -СН(СН3)2 и CF3;
R3 выбран из группы, состоящей из
Ar представляет собой арильную группировку, незамещенную или замещенную одной или более чем одной группировкой, независимо выбранной из группы, состоящей из (С1-С6)алкила, галогена, трифторметила, циано, нитро, гидрокси и -OR4;
Х выбран из группы, состоящей из –СН2-, -СН(СН3)-, -С(СН3)2-, -СН(ОН)-, -NH-, -N(СН3)-, -СН2СН2-, -С(=O)-, -S- и -О-;
когда Ar представляет собой фенил или шестичленную гетероароматическую кольцевую систему, Х расположен на кольце Ar в положении 1,4 по отношению к группе -O-R2;
когда Ar представляет собой 5-членную гетероароматическую кольцевую систему, Х расположен на кольце Ar в положении 1,3 по отношению к группе -O-R2;
R4 независимо выбран из группы, состоящей из -Н и -(С1-С6)алкила;
R5 независимо выбран из группы, состоящей из -Н, -(С1-С6)алкила и -(С2-С6)алкенила; и
R6 независимо выбран из группы, состоящей из -Н, -(С1-С6)алкила,-(С2-С6)алкенила и гетероарила,
где указанный гетероарил является незамещенным или замещен -(С1-С6)алкилом.
3. Соединение по п.1, где
R1 выбран из группы, состоящей из циклопропилметила, этила, пропила, аллила, изопентила, бензила, метоксиэтила, диметиламиноэтила, 4-пиридилметила, 2-пиридилметила, 1-пирролилэтила, 1-морфолиноэтила, 5-(2-метилтиазолила), циклогексилметила, 2-пирролидилметила, N-метил-2-пирролидилметила, 2-пиперидилметила, N-метил-2-пиперидилметила, 3-тиенилметила, 2-тетрагидрофуранилметила, (2-нитротиофен-5-ил)метила, (1-метил-1Н-имидазол-2-ил)метила, (5-(ацетоксиметил)-2-фуранил)метила, (2,3-дигидро-1Н-изоиндол-1-ил)метила и 5-(2-метилтиазолила);
R2 выбран из группы, состоящей из –СН3, -СН2СН3, -СН(СН3)2 и CF3;
R4 представляет собой -(С1-С6)алкил;
R5 выбран из группы, состоящей из -Н, -СН3, -СН2СН3, -СН=СН2 и -СН2-СН=СН2;
R6 выбран из группы, состоящей из –СН3, -СН2СН3, -СН=СН2, -СН2-СН=СН2, -CH2-CH2-CH=CH2, -СН2СН(СН3)2 и 5-метил-3-изоксазола;
Ar представляет собой фенил или шестичленную гетероароматическую кольцевую систему, каждый из которых может быть незамещенным или замещенным одной или более чем одной группировкой, независимо выбранной из группы, состоящей из -(С1-С6)алкила, галогена, трифторметила, циано, нитро, гидрокси и -OR4;
Х выбран из группы, состоящей из -СН2-, -СН2СН2-, -S-, -О-, -СН(СН3)-, -С(СН3)2, -СН(ОН)-, -NH-, -N(СН3)- и -С(=O)-; и
Х расположен на кольце Ar в положении 1,4 относительно группы -O-R2.
4. Соединение по п.1, где
R2 представляет собой –CH2CH3;
Ar представляет собой незамещенный фенил или пиридил;
Х выбран из группы, состоящей из -СН2-, -СН2СН2-, -S-, -СН(СН3)-, -С(СН3)2, -СН(ОН)-, -NH-, -N(СН3)- и -О-;
Х расположен на кольце Ar в положении 1,4 относительно группы -O-R2; и
R4 представляет собой метил.
5. Соединение формулы I по любому из пп.1-4 для применения в лечении.
6. Соединение по п.5, где лечение представляет собой лечение боли.
7. Применение соединения по п.1 для изготовления лекарственного средства для использования в лечении боли.
8. Фармацевтическая композиция, включающая в себя соединение по п.1 в качестве активного ингредиента совместно с фармацевтически приемлемым носителем.
9. Способ лечения боли у теплокровного животного, при котором указанному животному, нуждающемуся в таком лечении, вводят терапевтически эффективное количество соединения формулы I по п.1.
10. Способ избирательного восстановления группировки нитро, находящейся в положении орто относительно заместителя амино на фенильном или пиридильном кольце соединения, в присутствии группировки нитро, находящейся в положении пара относительно заместителя амино на фенильном или пиридильном кольце соединения, при котором обрабатывают раствор соединения в растворителе палладиевым катализатором в присутствии водорода.
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| SE0101387A SE0101387D0 (sv) | 2001-04-20 | 2001-04-20 | Novel compounds |
| SE0101387-9 | 2001-04-20 |
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| SE0302572D0 (sv) * | 2003-09-26 | 2003-09-26 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
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| AU2005287429A1 (en) * | 2004-09-24 | 2006-03-30 | Astrazeneca Ab | Compounds, compositions containing them, preparations thereof and uses thereof II |
| WO2006033632A1 (en) * | 2004-09-24 | 2006-03-30 | Astrazeneca Ab | Benzimidazole derivatives and their use as cannabinoid receptor ligands I |
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| US2945044A (en) * | 1957-07-12 | 1960-07-12 | Ciba Pharm Prod Inc | Certain 1-(diethyl-aminoethyl), 5-amino, 2-benzyl or substituted benzyl, benzimidazoles |
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| NZ288608A (en) * | 1994-06-10 | 1999-01-28 | Byk Gulden Lomberg Chem Fab | Substituted pyridinylmethyl-thio(or sulphinyl)-benzimidazole(or 1h-imidazo-[2,3-b]-pyridine) and medicaments to combat heliobacter bacteria |
| SE0203070D0 (en) * | 2002-10-16 | 2002-10-16 | Astrazeneca Ab | Novel compounds |
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| Publication number | Publication date |
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| US7030139B2 (en) | 2006-04-18 |
| WO2002085866A1 (en) | 2002-10-31 |
| BG108271A (bg) | 2004-12-30 |
| SK13032003A3 (sk) | 2005-01-03 |
| US20060135554A1 (en) | 2006-06-22 |
| EE200300524A (et) | 2004-02-16 |
| ZA200307752B (en) | 2005-01-03 |
| UA76743C2 (ru) | 2006-09-15 |
| MXPA03009558A (es) | 2004-02-12 |
| EP1390350A1 (en) | 2004-02-25 |
| HUP0303825A2 (hu) | 2004-03-01 |
| NO20034665D0 (no) | 2003-10-17 |
| PL366517A1 (en) | 2005-02-07 |
| RU2312864C2 (ru) | 2007-12-20 |
| CA2444381A1 (en) | 2002-10-31 |
| JP2004528334A (ja) | 2004-09-16 |
| CN1250531C (zh) | 2006-04-12 |
| BR0208907A (pt) | 2004-04-20 |
| IS6971A (is) | 2003-09-29 |
| KR20040022421A (ko) | 2004-03-12 |
| AR035959A1 (es) | 2004-07-28 |
| CN1503787A (zh) | 2004-06-09 |
| US20040116465A1 (en) | 2004-06-17 |
| CZ20032833A3 (en) | 2004-05-12 |
| HUP0303825A3 (en) | 2005-06-28 |
| MY134568A (en) | 2007-12-31 |
| IL158142A0 (en) | 2004-03-28 |
| NO20034665L (no) | 2003-12-10 |
| NZ528403A (en) | 2005-05-27 |
| SE0101387D0 (sv) | 2001-04-20 |
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