New benzimidazole derivatives as antihistamine agents
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一种化合物、烷基的技术，应用在新型苯并咪唑衍生物领域，能够解决缺乏活性等问题
Active Publication Date: 2017-08-29
FAES FARMA SA
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The present invention relates to a group of novel compounds with benzimidazole structure, which have effective selective H 1 Antihistamine activity, lack of activity on the central nervous system and cardiovascular system
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Embodiment 1
[0102] Example 1. Synthesis of 2-(4-(1-(2-ethoxyethyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)ethan-1-ol
[0103]
[0104] 2-Ethoxyethyl 4-methylbenzenesulfonate (2.4 g, 9.7 mmol) and KOH (0.71 g, 13 mmol) were added to 2-(4-(1H-benzo[d]imidazol-2-yl )piperidin-1-yl)ethan-1-ol (Intermediate A, 1.6 g, 5.1 mmol) in 10 ml of DMF. The reaction was heated to 40-45°C with stirring for 5-6 hours. Water (15ml) was added, and the mixture was washed with CH 2 Cl 2 (3 x 10ml) extraction. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo to give an oil, which was subjected to flash chromatography (DCM / CH 3 OH 95:5) to afford 1 g (61.9% yield) of 2-(4-(1-(2-ethoxyethyl)-1H-benzo[d]imidazole-2- base) piperidin-1-yl) ethan-1-ol. 1 H-NMR (CDCl 3)7.7(m,1H),7.3-7.2(m,3H),4.3(t,2H),3.7(m,4H),3.4(c,2H),3.3-3.1(m,4H),2.7(m ,2H), 2.5(m,2H), 2.3-2.1(m,4H), 1.1(t,3H)ppm.
Embodiment 2
[0105] Example 2. 2-(1-(2-(2-ethoxyethoxy)ethyl)piperidin-4-yl)-1-(2-ethoxyethyl)-1H-benzo[ d] imidazole
[0106] In the same experiment as in Example 1 above, 0.3 g (15% yield) of the compound of Example 2 was also obtained in the form of a yellow oil. 1 H-NMR (CDCl 3 )7.7(m,1H),7.3-7.2(m,3H),4.3(t,2H),3.7(m,4H),3.4(c,2H),3.3-3.1(m,4H),2.7(m ,2H), 2.5(m,2H), 2.3-2.1(m,4H), 1.1(t,3H)ppm.
Embodiment 3
[0108] Example 3. 3-(4-(1-(2-ethoxyethyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)propan-1-ol. From the middle Body B and 2-ethoxyethyl 4-methylbenzenesulfonate
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Abstract
The invention relates to compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof, a method of synthesis of said compounds, pharmaceutical compositions comprising them and their use in the treatment and / or prevention of conditions mediated by H1 histamine receptor, such as allergic disorders or diseases.
Description
technical field [0001] The present invention relates to novel benzimidazole derivatives, methods of synthesis, pharmaceutical compositions containing them and their use as antihistamine and antiallergic agents. Background technique [0002] It has long been known that histamine plays a very important role in allergic diseases such as allergic rhinitis, conjunctivitis, rhinoconjunctivitis, dermatitis, urticaria and asthma. Histamine H 1 - Antihistamine compounds acting at the receptor level are used to treat such symptoms. [0003] The first generation H 1 Antihistamines produce many adverse effects due to their effects on the central nervous system and cholinergic receptors. [0004] The search for molecules that do not cross the blood-brain barrier has led to the replacement of earlier antihistamines by other second-generation antihistamines that overcome the side effects associated with their effects on the central nervous system. More recently, this new generation of ...
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