3-methyl-5-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-5-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine
• 英文别名: 2-(5-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-4H-imidazol-5-ol
• 化学式: C₁₇H₁₆F₃N₃O₃S
• 分子量: 399.394
• InChiKey: HWXJMNGCVXATHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  91.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-methyl-5-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine 在 对甲苯磺酸一水合物 作用下， 以 甲苯 为溶剂， 以47%的产率得到3-methyl-5-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine
  参考文献：
  名称：

  1,2-aryl and heteroaryl substituted imidazolyl compounds for the

  摘要：

  描述了一类咪唑基化合物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由以下式I定义：##STR1##其中R.sup.1 -R.sup.6如规范中所述；或其药用盐。

  公开号：

  US05616601A1
• 作为产物：
  描述：

  N-[4-(methylsulfonyl)phenyl]-5-methylnicotinamidine 、 3-溴-1,1,1-三氟丙酮 在 碳酸氢钠 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以25%的产率得到3-methyl-5-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine
  参考文献：
  名称：

  A process for the preparation of 4-¬2-(aryl or heterocyclo)-1H-imidazol-1-yl|benzenesulfonamides

  摘要：

  公开号：

  EP1193265B1

文献信息

• 1,2-aryl and heteroaryl substituted imidazolyl compounds for the
  申请人：GD Searle & Co

  公开号：US05616601A1

  公开（公告）日：1997-04-01

  A class of imidazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I: ##STR1## wherein R.sup.1 -R.sup.6 are as described in the specification; or a pharmaceutically-acceptable salt thereof.

  描述了一类咪唑基化合物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由以下式I定义：##STR1##其中R.sup.1 -R.sup.6如规范中所述；或其药用盐。
• Heterocyclo-substituted imidazoles for the treatment of inflammation
  申请人：Khanna K. Ish

  公开号：US20050096368A1

  公开（公告）日：2005-05-05

  A class of imidazolyl compounds is described for use in treating inflammation. Compounds of particular interest are defined by formula (V), wherein R 3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, heteroaralkyl, acyl, cyano, alkoxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclocarbonyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, alkylaminocarbonylalkyl, heteroarylalkoxyalkyl, heteroaryloxyalkyl, heteroarylthioalkyl, aralkoxy, aralkylthio, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, arylthio, aryloxy. aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl; wherein R 4 is a radical selected from hydrido, alkyl and halo; and wherein R 13 and R 14 are independently selected from aryl and heterocyclo, wherein R 13 and R 14 are optionally substituted at a substitutable position with one or more radicals independently selected from alkylsulfonyl, aminosulfonyl, halo, alkylthio, alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkoxy, amino, alkylamino, arylamino and nitro; provided at least one of R 13 and R 14 is aryl substituted with alkylsulfonyl or aminosulfonyl; or a pharmaceutically-acceptable salt thereof.

  描述了一类咪唑基化合物用于治疗炎症。特别感兴趣的化合物由公式（V）定义，其中R3是从氢基，烷基，卤代烷基，芳基烷基，杂环烷基，杂环芳基烷基，酰基，氰基，烷氧基，烷硫基，烷硫基烷基，烷基磺酰基，环烷硫基，环烷硫基烷基，环烷磺酰基，环烷磺酰基烷基，卤代烷基磺酰基，芳基磺酰基，卤代基，羟基烷基，烷氧基烷基，烷基羧酰基，芳基羧酰基，芳基烷基羧酰基，杂环羧酰基，氰基烷基，氨基烷基，烷基氨基烷基，N-芳基氨基烷基，N-烷基-N-芳基氨基烷基，羧基烷基，烷氧基羧酰基烷基，烷氧基羧酰基，卤代烷基羧酰基，羧基，氨基羧酰基，烷基氨基羧酰基，杂环芳基烷氧基烷基，杂环芳基氧基烷基，杂环芳基硫基烷基，芳基硫醇基烷基，芳基氧基烷基，芳基硫醇基，芳基氧基。芳基烷硫基烷基，芳基烷氧基烷基，芳基和杂环芳基;其中R4是从氢基，烷基和卤代基中选择的基团;并且R13和R14分别从芳基和杂环芳基中选择，其中R13和R14在可取代位置上可以选择一个或多个基团独立地选择，包括烷基磺酰基，氨基磺酰基，卤代基，烷硫基，烷基，氰基，羧基，烷氧基羧酰基，卤代烷基，羟基，烷氧基，羟基烷基，烷氧基烷基，卤代烷氧基，氨基，烷基氨基，芳基氨基和硝基; 提供至少一个R13和R14被烷基磺酰基或氨基磺酰基取代的芳基，或其药学上可接受的盐。
• Olefin polymerization catalyst having a multidentate ligand
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0617052A2

  公开（公告）日：1994-09-28

  Disclosed is an olefin polymerization catalyst comprising a transition metal selected from metals of Groups IIIA including the lanthanide series, IVA, VA, VIA, VIIA and VIII of the Periodic Table of the Elements, and ligands L¹ and L² bonded thereto, wherein a combination of L¹ and L² is (1) a combination of ligand L¹ which is a group containing at least one phosphorus-containing group and ligand L² which is a ligand having a σ-bond, or a ligand having a σ-bond and a bond selected from at least one π-bond and at least one lone electron pair donative bond; (2) a combination of ligand L¹ which is a 5-membered heterocyclic pentadentate ligand having one or more heteroatoms and ligand L² which is a ligand having a σ-bond, or a ligand having a σ-bond and a bond selected from at least one π-bond and at least one lone electron pair donative bond, provided that when the pentadentate ligand contains only one heteroatom, L² is a ligand having a σ-bond, or a ligand having a σ-bond and at least one lone electron pair donative bond; and (3) a combination of ligand L¹ which is a trispyrazolyl tridentate ligand and ligand L² which is an alkapolyenyl ligand, and wherein each L¹ contains an element of Group VB or Group VIB. The catalyst of the present invention has extremely high catalytic activity for an olefin polymerization reaction as compared to conventional olefin polymerization catalysts.

  本发明公开了一种烯烃聚合催化剂，该催化剂包含选自元素周期表中包括镧系在内的IIIA族、IVA族、VA族、VIA族、VIIA族和VIII族金属的过渡金属，以及与其结合的配体L¹和L²、其中 L¹ 和 L² 的组合是 (1) 配体 L¹ 是含有至少一个含磷基团的基团，配体 L² 是具有 σ 键的配体，或具有 σ 键和选自至少一个 π 键和至少一个孤电子对捐赠键的键的配体的组合；(2) 配体 L¹ 的组合，配体 L¹ 是具有一个或多个杂原子的五元杂环配体，配体 L² 是具有σ键的配体，或具有σ键和选自至少一个π键和至少一个孤电子对捐赠键的配体、条件是当五价配体只含有一个杂原子时，L² 是具有一个 σ 键的配体，或具有一个 σ 键和至少一个孤电子对捐赠键的配体；和 (3) 配体 L¹（三异吡唑三叉配体）和配体 L²（烷基多烯配体）的组合，其中每个 L¹ 包含一个 VB 族或 VIB 族元素。与传统的烯烃聚合催化剂相比，本发明的催化剂对烯烃聚合反应具有极高的催化活性。
• A process for the preparation of 4-[2-(aryl or heterocyclo)-1H-imidazol-1-yl]benzenesulfonamides
  申请人：G.D. Searle & Co.

  公开号：EP1193265A2

  公开（公告）日：2002-04-03

  A process to make a compound of the formula or a pharmaceutically acceptable salt thereof is disclosed wherein R3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, heteroaralkyl, acyl, cyano, alkaxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclocarbonyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, alkylaminocarbonylalkyl, heteroarylalkoxyalkyl, heteroaryloxyalkyl, heteroarylthioalkyl, aralkoxy, aralkylthio, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, arylthio, aryloxy, aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl; wherein R4 is a radical selected from hydrido, alkyl and halo; and wherein R2 is selected from aryl and heterocyclo, wherein R2 is optionally substituted at a substitutable position with one or more radicals independently selected from alkylsulfonyl, aminosulfonyl, halo, alkylthio, alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkoxy, amino, alkylamino, arylamino and nitro;    said method comprising the steps of forming a (protected sulfonyl)benzenamine, treating said (protected sulfonyl)benzenamine first with a base and then with a nitrile to form an amidine, treating said amidine with a haloketone derivative in the presence of a base to form a hydroxyimidazole, forming a (protected sulfonylphenyl) imidazole by dehydrating said hydroxyimidazole, and forming said compounds by deprotecting said (protected sulfonylphenyl)imidazole.

  本发明公开了一种制备式 或其药学上可接受的盐的工艺。 其中 R3 是选自氢基、烷基、卤代烷基、芳基、杂环烷基、杂芳基、酰基、氰基、烷氧基、烷硫基、烷硫基、烷基磺酰基、环烷硫基、环烷硫基、环烷基磺酰基、环烷基磺酰基、卤代烷基磺酰基、芳基磺酰基、卤代烷基磺酰基、卤代芳基磺酰基、卤代芳基磺酰基、环烷基磺酰基、卤代烷基磺酰基、芳基磺酰基、卤代、羟基烷基、烷氧基烷基、烷基羰基、芳基羰基、芳基羰基、杂环羰基、氰基烷基、氨基烷基、烷基氨基烷基、N-芳基氨基烷基、N-烷基-N-芳基氨基烷基、羧基、烷氧基羰基、烷氧羰基、卤代烷基羰基、羧基、氨基羰基、烷基氨基羰基、烷基氨基羰基烷基、杂芳基烷氧基烷基、杂芳氧基烷基、杂芳硫基烷基、杂芳基硫代烷基、杂芳基硫代烷基、杂芳基氧基烷基、杂芳基硫代烷基、芳基硫代烷基、芳基氧基烷基、芳基硫代烷基、芳基氧基烷基、芳基硫代烷基、芳基烷氧基烷基、芳基和杂芳基；其中 R4 是选自氢基、烷基和卤代的基团；以及 其中 R2 选自芳基和杂环基，其中 R2 在可取代的位置上任选被一个或多个独立选自烷基磺酰基、氨基磺酰基、卤代基、烷硫基、烷基、氰基、羧基、烷氧基羰基、卤代烷基、羟基、烷氧基、羟基烷基、烷氧基烷基、卤代烷氧基、氨基、烷基氨基、芳基氨基和硝基的基团取代； 所述方法包括以下步骤：形成(受保护的磺酰基)苯胺，首先用碱处理所述(受保护的磺酰基)苯胺，然后用腈处理以形成脒，在碱存在下用卤代酮衍生物处理所述脒以形成羟基咪唑，通过使所述羟基咪唑脱水形成(受保护的磺酰基苯基)咪唑，以及通过对所述(受保护的磺酰基苯基)咪唑进行脱保护形成所述化合物。
• [EN] 1,2-SUBSTITUTED IMIDAZOLYL COMPOUNDS FOR THE TREATMENT OF INFLAMMATION<br/>[FR] COMPOSES D'IMIDAZOLYLE SUBSTITUES EN POSITIONS 1 ET 2, CONVENANT AU TRAITEMENT DE L'INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：WO1996003388A1

  公开（公告）日：1996-02-08

  (EN) A class of imidazolyl compounds is described for use in treating inflammation. Compounds of particular interest are defined by formula (II), wherein R3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, acyl, cyano, alkoxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkyloxy, cycloalkyloxyalkyle, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cyanoalkyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, azidoalkyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, arylthio, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, aryloxy, heterocycloalkylcarbonyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonylalkyl, aralkylthio, heteroarylalcoxyalkyl, heteroaryloxyalkyl, aralkoxy, heteroarylthioalkyl, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl, wherein the aryl and heteroaryl radicals are optionally substitued at a substitutable position with one or more radicals selected from halo, alkylthio, alkylsufinyl, alkyl, cyano, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl and haloalkoxy; wherein R7 is a radical selected from alkyl and amino; and wherein R8 is one or more radicals selected from hydrido, halo, alkyl, haloalkyl, alkoxy, amino, haloalkoxy, cyano, carboxyl, hydroxyl, hydroxyalkyl, alkoxyalkyl, alkylamino, nitro and alkylthio.(FR) La présente invention concerne une classe de composés d'imidazolyle convenant au traitement de l'inflammation. Les composés concernés en l'occurrence sont décrits par la formule générale (II). Dans cette formule générale (II), 'R3' représente un radical choisi parmi hydrido, alkyle, haloalkyle, aralkyle, hétérocycloalkyle, acyle, cyano, alcoxy, alkylthio, alkylthioalkyle, alkylsulfonyle, cycloalkyloxy, cycloalkyloxyalkyle, cycloalkylthio, cycloalkylthioalkyle, cycloalkylsulfonyle, cyanoalkyle, cycloalkylsulfonylalkyle, haloalkylsulfonyle, azidoalkyle, arylsulfonyle, halo, hydroxyalkyle, alcoxyalkyle, arylthio, alkylcarbonyle, arylcarbonyle, aralkylcarbonyle, aryloxy, hétérocycloalkylcarbonyle, alkylaminoalkyle, N-arylaminoalkyle, N-alkyl-N-arylaminoalkyle, carboxyalkyle, alcoxycarbonylalkyle, alcoxycarbonyle, haloalkylcarbonyle, aminocarbonyle, alkylaminocarbonylalkyle, aralkylthio, hétéroarylalcoxyalkyle, hétéroaryloxyalkyle, aralcoxy, hétéroarylthioalkyle, hétéroaralcoxy, hétéroaralkylthio, hétéroarylalkylthioalkyle, hétéroaryloxy, hétéroarylthio, arylthioalkyle, aryloxyalkyle, aralkylthioalkyle, aralcoxyalkyle, aryle et hétéroaryle, les radicaux aryle et hétéroaryle étant éventuellement substitués à des positions admettant la substitution par au moins un radical choisi parmi halo, alkylthio, alkylsulfinyle, alkyle, cyano, haloalkyle, hydroxyle, alcoxyle, hydroxyalkyle et haloalcoxy. 'R7' représente un radical choisi parmi alkyle et amino. 'R8' représente au moins un radical choisi parmi hydrido, halo, alkyle, haloalkyle, alcoxy, amino, haloalcoxy, cyano, carboxyle, hydroxyle, hydroxyalkyle, alcoxyalkyle, alkylamino, nitro et alkylthio.

  描述了一类咪唑基化合物，用于治疗炎症。特别感兴趣的化合物由式(II)表示，其中R3为选自氢、烷基、卤代烷基、芳烷基、杂环烷基、酰基、氰基、烷氧基、烷硫基、烷硫基烷基、烷基磺酰基、环烷氧基、环烷氧基烷基、环烷硫基、环烷硫基烷基、环烷基磺酰基、氰基烷基、环烷基磺酰基烷基、卤代烷基磺酰基、硝基烷基、芳基磺酰基、卤素、羟基烷基、烷氧基烷基、芳硫基、烷基羰基、芳基羰基、芳烷基羰基、 aryloxy、杂环烷基羰基、烷基氨基烷基、N-芳基氨基烷基、N-烷基-N-芳基氨基烷基、羧基烷基、烷氧羰基烷基、烷氧羰基、卤代烷基羰基、氨基羰基、烷基氨基羰基烷基、芳烷硫基、杂环烷基羰基烷基、杂芳基氧基烷基、杂芳氧基烷基、芳烷氧基、杂芳基硫代烷基、杂芳烷氧基、杂芳烷硫基、杂芳基烷硫基烷基、杂芳氧基、杂芳基硫基、芳基硫代烷基、芳氧基烷基、芳烷硫基烷基、芳烷氧基烷基、芳基和杂芳基的基团，其中所述芳基和杂芳基基团在可取代的位置上任选地被一个或多个卤素、烷基硫基、烷基磺酰基、烷基、氰基、卤代烷基、羟基、烷氧基、羟基烷基和卤代烷氧基取代；其中R7为选自烷基和氨基的基团；并且R8为一个或多个选自氢、卤素、烷基、卤代烷基、烷氧基、氨基、卤代烷氧基、氰基、羧基、羟基、羟基烷基、烷氧基烷基、烷基氨基、硝基和烷基硫基的基团。