1-[6-(4-carbamylphenoxy)hexyl]imidazole hydrochloride | 134789-49-4

• 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: 1-[6-(4-carbamylphenoxy)hexyl]imidazole hydrochloride
• 英文别名: 4-(6-Imidazol-1-ylhexoxy)benzamide;hydrochloride
• CAS: 134789-49-4
• 化学式: C₁₆H₂₁N₃O₂*ClH
• 分子量: 323.823
• InChiKey: RANJHUYWXNIZQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  3

文献信息

• Pharmaceutically active compounds
  申请人：SCHERING CORPORATION

  公开号：EP0407217A1

  公开（公告）日：1991-01-09

  The disclosed invention is compounds represented by the formula and pharmaceutically acceptable acid addition, basic addition and quarternary amine salts thereof and pharmaceutically acceptable solvates thereof, wherein each Z is independently tetiary butyl, phenyl, naphthyl or adamantyl: substituted phenyl, wherein the substituents are one or more of halogen, lower alkoxy, phenoxy, nitrile, nitro, phenylsulfonyl, loweralkylsulfonyl, oxazol-2-yl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, lower alkyl, lower alkylthio, phenyl. phenylaminothiocarbonyl, or lower alkylaminothiocarbonyl, hydroxyiminoloweralkyl hydroxyloweralkyl or carbonyl; or 4 or 6 membered unsubstituted or substituted heterocyclic ring containing at least one nitrogen with the remaining member of the ring being at least one carbon, and optionally sulfur or oxygen, wherein the substituents are one or more of carboxyl, hydroxymethyl, lower alkyl, loweralkylcarbonyl or aryl lower alkyl; X and Y are each independently a bond, -0-, each Q is independently a divalent substituted or unsubstituted, straight or branched chain lower alkanediyl. lower alkanediyl-cycloalkanediyl-lower alkanediyl, lower alkenediyl, lower alkynediyl, phenylene, dihydrofurandiyl, loweralkanediyl-dihydrofurandiyl-loweralkanediyl, tetrahydrofurandiyl, tetrahydropyrandiyl, loweralkanediyl- tetrahydropyrandlyl-loweralkanediyl or, loweralkanediyl-tetrahydrofurandiyl-loweralkanediyl, wherein the substituents are one or more of hydroxy, ketalized adjacent hydroxys, epoxy, fluorine, chlorine, azide, or amino; W is a monovalent substituted or unsubstituted aryl group or a heterocyclic single or fused ring containing from 4 to 10 ring atoms, at least one hetero atom of which is a nitrogen atom and the remaining ring atoms being at least one carbon and optionally sulfur or oxygen, wherein the substituents are one or more of hydroxy, oxo amino, carbamoyl, carboxyl, nitrile, nitro, lower alkoxy carbonyl, halogen, sulfamyl, lower alkyl, lower alkylthio, lower alkoxy, hydroxyloweralkyl, lower alkoxycarbonylloweralkyl, amino loweralkyl, carboxyloweralkyl, guanidino, thioureido, lower alkylsulfonylamino, aminocarbonylloweralkyl, allyloxycarbonylmethyl or carbamoyloxyloweralkyl; with the proviso that W cannot be substituted or unsubstituted isoxazolyl, andwith the further proviso that when Z is 2-chloro-4-methoxyphenyl, X is -0-, Q is Cs-C1 alkanediyl and Y is a bond, W is not imidazolyl substituted at position 2, 4 and 5 with 1-3 substituents independently selected from the group consisting of hydrogen, hydroxyloweralkyl, nitro, loweralkoxycarbonyl, lower alkyl and amino methylene; W' is divalent W. The compounds have antiviral activity, antiinflammatory activity and are PAF inhibitors.

  本发明公开了由以下式子表示的化合物 及其药学上可接受的酸加成盐、碱加成盐和季胺盐以及药学上可接受的溶液，其中每个 Z 独立地为四叔丁基、苯基、萘基或金刚烷基：取代的苯基，其中取代基为卤素、低级烷氧基、苯氧基、腈基、硝基、苯磺酰基、低级烷基磺酰基、噁唑-2-基、低级烷酰基、苯甲酰基、低级烷氧基羰基、低级烷基、低级烷硫基、苯基中的一个或多个。苯基氨基硫代羰基，或低级烷基氨基硫代羰基，羟基亚氨基低级烷基羟基低级烷基或羰基；或 4 或 6 个成员的未取代或取代的杂环，环中至少含有一个氮，环的其余成员至少含有一个碳，以及可选的硫或氧，其中取代基为羧基、羟甲基、低级烷基、低级烷基羰基或芳基低级烷基中的一个或多个；X 和 Y 各自独立地为键、-0-、 每个 Q 独立地为二价取代或未取代的直链或支链低级烷二基。低级烷二基-环烷二基-低级烷二基、低级烯二基、低级炔二基、亚苯基、二氢呋喃二基、低级烷二基-二氢呋喃二基-低级烷二基、四氢呋喃二基、四氢吡喃二基、低级烷二基-四氢吡喃-低级烷二基或低级烷二基-四氢呋喃二基-低级烷二基， 其中取代基为羟基、酮化邻接羟基、环氧基、氟、氯、叠氮化物或氨基中的一个或多个；W 是一价取代或未取代的芳基，或含有 4 至 10 个环原子的杂环，其中至少一个杂原子为氮原子，其余环原子至少为一个碳原子，可选为硫或氧原子，其中取代基为羟基、氧氨基、氨基甲酰基、羧基中的一个或多个、氨基甲酰基、羧基、腈基、硝基、低级烷氧基羰基、卤素、氨基磺酰基、低级烷基、低级烷硫基、低级烷氧基、羟基低级烷基、低级烷氧基羰基低级烷基、氨基低级烷基、羧基低级烷基、胍基、硫脲基、低级烷基磺酰基氨基、氨基羰基低级烷基、烯丙基氧羰基甲基或氨基甲酰氧羰基低级烷基中的一种或多种；但条件是 W 不能是取代或未取代的异噁唑基，进一步的但条件是当 Z 是 2-氯-4-甲氧基苯基、X 是-0-、Q 是 Cs-C1 烷二基和 Y 是键时，W 不是在第 2、4 和 5 位被 1-3 个独立选自氢、羟基低级烷基、硝基、低级烷氧基羰基、低级烷基和氨基亚甲基的取代基取代的咪唑基；W'是二价 W。 这些化合物具有抗病毒活性和抗炎活性，并且是 PAF 抑制剂。
• US5272167A
  申请人：——

  公开号：US5272167A

  公开（公告）日：1993-12-21
• US5459144A
  申请人：——

  公开号：US5459144A

  公开（公告）日：1995-10-17
• [EN] PHARMACEUTICALLY ACTIVE COMPOUNDS
  申请人：SCHERING CORPORATION

  公开号：WO1991000858A1

  公开（公告）日：1991-01-24

  (EN) The disclosed invention relates to compounds represented by the formula (I): Z-X-Q-Y-W, (II): Z-X-Q-Y-W'-Y-Q-X-Z and pharmaceutically acceptable salts thereof, wherein each Z is independently tertiary butyl, phenyl, naphthyl or adamantyl; substituted phenyl, or 4 or 6 membered unsubstituted or substituted heterocyclic ring containing at least one nitrogen with the remaining member of the ring being at least one carbon, and optionally sulfur or oxygen; X and Y are each independently a bond, -O-, -S-, -SO2-, (a), (b), (c), (d), (e), (f), (g), (h) or -CH2-O-; each Q is independently a divalent substituted or unsubstituted, straight or branched chain lower alkanediyl, lower alkanediyl-cycloalkanediyl-lower alkanediyl, lower alkenediyl, lower alkynediyl, phenylene, dihydrofurandiyl, loweralkanediyl-dihydrofurandiyl-loweralkanediyl, tetrahydrofurandiyl, tetrahydropyrandiyl, loweralkanediyl-tetrahydropyrandiyl-loweralkanediyl or, loweralkanediyl-tetrahydrofurandiyl-loweralkanediyl, wherein the substituents are one or more of hydroxy, ketalized adjacent hydroxys, epoxy, fluorine, chlorine, azide, or amino; W is a monovalent substituted or unsubstituted aryl group or a heterocyclic single or fused ring, at least one hetero atom of which is a nitrogen atom and the remaining ring atoms being at least one carbon and optionally sulfur or oxygen, with the proviso that W cannot be substituted or unsubstituted isoxazolyl, and with the further proviso that when Z is 2-chloro-4-methoxyphenyl, X is -O-, Q is C5-C7 alkanediyl and Y is a bond, W is not imidazolyl substituted at positions 2, 4 and 5 with 1-3 substituents independently selected from the group consisting of hydrogen, hydroxyloweralkyl, nitro, loweralkoxycarbonyl, lower alkyl and amino methylene; W' is divalent W. The compounds have antiviral activity, antiinflammatory activity and are PAF inhibitors.(FR) L'invention concerne des composés représentés par les formules (I) Z-X-Q-Y-W, (II) Z-X-Q-Y-W'-Y-Q-X-Z, ainsi que leurs sels acceptables en pharmacologie dans lesquels chaque Z représente indépendamment butyle, phényle, naphtyle ou adamantyle tertiaire; phényle substitué ou un anneau hétérocyclique non substitué ou substitué à 4 ou à 6 éléments contenant au moins un atome d'azote, l'élément restant de l'anneau étant au moins un atome de carbone, et facultativement du soufre ou de l'oxygène; X et Y représentent chacun indépendamment une liaison, -O-, -S-, -SO2-, (a), (b), (c), (d), (e), (f), (g), (h), ou -CH2-O-; chaque Q représente indépendamment alcanediyle inférieur, alcanediyle inférieur d'alcanediyle-cycloalcanediyle inférieur, alcènediyle inférieur, alkynediyle inférieur, phénylène, dihydrofurandiyle, alcanediyle inférieur-dihydrofurandiyle-alcanediyle inférieur, tétrahydrofurandiyle, tétrahydropyrandiyle, alcanediyle inférieur-tétrahydropyrandiyle-alcanediyle inférieur ou alcanediyle inférieur-tétrahydrofurandiyle-alcanediyle divalents à chaînes droites ou ramifiées substitués ou non substitués dans lesquels les substituants sont un ou plusieurs des éléments suivants: hydroxy, hydroxy adjacents cétalisés, époxy, fluor, chlore, acide, ou amino; W représente un groupe aryle substitué ou non substitué monovalent ou un anneau individuel ou fusionné hétérocyclique, dont au moins un hétéroatome est un atome d'azote, les atomes cycliques restants étant au moins un atome de carbone et facultativement un atome de soufre ou d'oxygène, à condition que W ne puisse pas représenter isoxazolyle substitué ou non substitué, et également à condition que lorsque Z représente 2-chloro-4-méthoxyphényle, X représente -O-, Q représente alcanediyle contenant 5 à 7 atomes de carbone et Y représente une liaison, W ne soit pas à substitution imidazoyle aux positions 2, 4 et 5, 1 à 3 substituants étant indépendamment sélectionnés dans le groupe composé d'hydrogène, hydroxyalkyle inférieur, alkoxycarbonyle inférieur, alkyle inférieur et amino méthylène; W' représente W divalent. Les composés de l'invention présentent une activité antivirale, une activité anti-inflammatoire et sont des inhibiteurs de PAF.