2-hydroxypyridine methiodide | 63863-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-hydroxypyridine methiodide
• 英文别名: 1-methylpyridin-1-ium-2-ol;iodide
• CAS: 63863-86-5
• 化学式: C₆H₈NO*I
• 分子量: 237.04
• InChiKey: SENLRGPGOSFQIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.88
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  21.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-fluoro-1-methylpyridinium iodide 在 硫酸 、 sodium chloride 作用下， 生成 2-hydroxypyridine methiodide
  参考文献：
  名称：

  Hydrolyses of 2- and 4-fluoro N-heterocycles. 4. Proton inventories of the hydrolyses of 2-fluoro-1-methylpyridinium iodide, 4-fluoroquinaldine, and 2-chloro-1-methylpyrimidinium triflate

  摘要：

  Rate constants for the hydrolyses of 2-fluoro-1-methylpyridinium iodide (3), 4-fluoroquinaldine (4), and 2-chloro-1-methylpyrimidinium triflate (5) in 2 X 10(-3) M aqueous sulfuric acid, in D2O/D2SO4, and in mixed H2O/H2SO4-D2O/D2SO4 media are reported. Significant solvent deuterium kinetic isotope effects are evident, with k(H)/k(D) = 2.07 for 3, 1.62 for 4, and 2.12 for 5. The results of the proton inventories for the hydrolyses of 3 and 5 are best fit by a form of the Gross-Butler equation for three nearly equivalent sites with fractionation factors of 0.78. The proton inventory of 4 does not yield a unique solution to the Gross-Butler equation, but the results are also consistent with three transition state sites with nearly equal fractionation factors of 0.72-0.78, as well as an additional transition-state site with phi > 1 and a reactant site with phi less-than-or-equal-to 1. These proton inventories are consistent with mechanisms in which nucleophilic addition of water in the rate-determining step is assisted by proton-transfer to a second water molecule, with development of an "immature hydronium ion" in the transition state. Mechanism with cyclic proton transfer are also consistent, but are less satisfactory as hydrolysis routes.

  DOI：

  10.1021/jo00050a017

文献信息

• [EN] BENZOXAZOLE ACETONITRILES<br/>[FR] BENZOXAZOLE ACETONITRILES
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2005026159A1

  公开（公告）日：2005-03-24

  The present invention is related to benzoxazole acetonitriles as well as to pharmaceutical formulations containing such benzoxazole acetonitriles pof formula (I). Said benzoxazole acetonitriles are useful in the treatment of metabolic disorders mediated by insulin resistance or hyperglycernia, comprising diabetes type II, inadequate glucose tolerance, insulin resistance, obesity, polycystic ovary syndrome (PCOS). The present invention is furthermore related to methods of preparing benzoxazole acetonitriles (I). A is a pyrimidinyl.L is a secondary or tertiary amino group, or a 3-8 membered heterocycloalkyl, containing at least one heteroatom. selected from N, O, S or L is an acylarnino moiety.R1 is selected from the group comprising or consisting of hydrogen, sulfonyl, amino, CiC6-alkYl, C2-C6-alkenYl, C2-C6-alkynyl or Cl-C6-alkoxy, aryl, halogen, carboxy,aminocarbonyl, cyano or hydroxy.

  本发明涉及苯并噁唑乙腈，以及含有该苯并噁唑乙腈的药物配方（I）的制备方法。所述苯并噁唑乙腈在治疗由胰岛素抵抗或高甘油三酯引起的代谢紊乱方面具有用途，包括糖尿病II型、葡萄糖耐量不佳、胰岛素抵抗、肥胖、多囊卵巢综合征（PCOS）。A是嘧啶基。L是次级或三级氨基团，或者是含有至少一个来自N、O、S的杂原子的3-8环杂环烷基。R1选择自氢、磺酰基、氨基、CiC6-烷基、C2-C6-烯基、C2-C6-炔基、Cl-C6-烷氧基、芳基、卤素、羧基、氨基羰基、氰基或羟基。
• Fluorinated pyridine derivatives
  作者：Christopher M. Timperley、Mike Bird、Suzannah C. Heard、Stuart Notman、Robert W. Read、John E.H. Tattersall、Simon R. Turner

  DOI：10.1016/j.jfluchem.2005.05.004

  日期：2005.8

  react with I(CH2)3I, 3-fluoropyridine gave the bis-quaternary salt and 3,5-difluoropyridine yielded a mono-quaternary derivative. Both 3- and 4-(trifluoromethyl)pyridine furnished the bis-quaternary products in 53 and 55% yield, respectively. The bis-quaternary salts are potentially useful in the treatment of organophosphorus nerve agent poisoning.

  进行实验以确定F-和CF 3-取代的吡啶是否用碘甲烷（在THF中为1：1摩尔比）和1,3-二碘丙烷（在MeCN中为2：1摩尔比）进行季铵化。2-氟吡啶和2-（三氟甲基）吡啶即使长时间回流也不会与MeI反应，而3-氟吡啶，3,5-二氟吡啶，3-（三氟甲基）吡啶和4-（三氟甲基）吡啶在28-产率72％。2-氟吡啶不与I（CH 2）3反应I，3-氟吡啶得到双季盐，而3，5-二氟吡啶得到单季衍生物。3-和4-（三氟甲基）吡啶分别以53％和55％的产率提供了双季产物。双季盐可潜在地用于治疗有机磷神经毒剂中毒。
• PROCESS FOR THE PREPARATION OF DIPHENYL AZETIDINONE DERIVATIVES
  申请人：Jendralla Joachim- Heiner

  公开号：US20070149501A1

  公开（公告）日：2007-06-28

  The present invention is a process for the preparation of diphenylazetidinone derivatives of the formula (I) or forms thereof comprising the substituents X, R 1 and/or R 2 as defined herein. More specifically, the invention comprises methods for the preparation of these compounds by cyclization of certain □-amino carboxamides or □-amino carboxylic esters. These diphenylazetidinone compounds are useful in the treatment of high blood serum cholesterol levels and the maintenance of the reduced cholesterol levels achieved thereby.

  本发明涉及一种制备式(I)的二苯基氮代氮杂环丙酮衍生物或其形式的方法，其中含有此处定义的取代基X、R1和/或R2。更具体地，本发明涉及通过某些□-氨基羧酰胺或□-氨基羧酸酯的环化制备这些化合物的方法。这些二苯基氮代氮杂环丙酮化合物在治疗高血清胆固醇水平和维持由此达到的降低胆固醇水平方面是有用的。
• [EN] HYDROXY-SUBSTITUTED AZETIDINONE COMPOUNDS USEFUL AS HYPOCHOLESTEROLEMIC AGENTS<br/>[FR] COMPOSES D'AZETIDINONE HYDROXY-SUBSTITUES EFFICACES EN TANT QU'AGENTS HYPOCHOLESTEROLEMIQUES
  申请人：SCHERING CORPORATION

  公开号：WO1995008532A1

  公开（公告）日：1995-03-30

  (EN) Hydroxy-substituted azetidinone hypocholesterolemic agents of formula (Ia) or a pharmaceutically acceptable salt thereof, wherein: Ar1 and Ar2 are aryl or R4-substituted aryl; Ar3 is aryl or R5-substituted aryl; X, Y and Z are -CH2-, -CH(lower alkyl)- or -C(dilower alkyl)-; R and R2 are -OR6, -O(CO)R6, -O(CO)OR9 or -O(CO)NR6R7; R1 and R3 are H or lower alkyl; q is 0 or 1; r is 0 or 1; m, n and p are 0-4; provided that at least one of q and r is 1, and the sum of m, n, p, q and r is 1-6; and provided that when p is 0 and r is 1, the sum of m, q and n is 1-5; R4 is selected from lower alkyl, R5, -CF3, -CN, -NO2 and halogen; R5 is selected from -OR6, -O(CO)R6, -O(CO)OR9, -O(CH2)1-5OR6,-O(CO)NR6R7, -NR6R7, -NR6(CO)R7, -NR6(CO)OR9, -NR6(CO)NR7R8, -NR6SO2R9, -COOR6, -CONR6R7, -COR6, -SO2NR6R7, S(O)0-2R9, -O(CH2)1-10-COOR6, -O(CH2)1-10CONR6R7, -(lower alkylene)COOR6 and -CH=CH-COOR6; R6, R7 and R8 are H, lower alkyl, aryl, or aryl-substituted lower alkyl; R9 is lower alkyl, aryl or aryl-substituted lower alkyl; are disclosed, as well as a method of lowering serum cholesterol by administering said compounds, alone or in combination with a cholesterol biosynthesis inhibitor, pharmaceutical compositions containing them, and a process for preparing them.(FR) Agents hypocholestérolémiques à base d'azétidinone hydroxy-substitués representés par la formule (Ia) ou un de leurs sels acceptables pharmaceutiquement, formule dans laquelle: Ar1 et AR2 représentent aryle ou akyle substitué par R4; Ar3 représente aryle ou aryle substitué par R5; X, Y et Z représentent -CH2-, -CH(alkyle inférieur) ou -C(alkyle di-inférieur)-; R et R2 représentent -OR6, -O(CO)R6, -O(CO)OR9 ou -O(CO)NR6R7; R1 et R3 représentent H ou alkyle inférieur; q est 0 ou 1; r est 0 ou 1; m, n, et p sont 0-4; dans la mesure ou au moins un de q et r est 1 et la somme de m, n, p, q et r est 1-6 et dans la mesure où quand p est 0 et r est 1, alors la somme de m, q et n est 1-5; R4 est sélectionné parmi alkyle inférieur, R5, -CF3, -CN, -NO2 et halogène; R5 est sélectionné parmi -OR6, -O(CO)R6, -O(CO)OR9, -O(CH2)1-5OR6, -O(CO)NR6R7, -NR6R7, -NR6(CO)R7, -NR6(CO)OR9, -NR6(CONR7R8, -NR6SO2R9, -COOR6, CONR6R7, -COR6, -SO2NR6R7, S(O)0-2R9, -O(CH2)1-10-COOR6, -O(CH2)1-10CONR6R7, -(alkylène inférieur)COOR6 et -CH=CH-COOR6; R6, R7 et R8 représentent H, alkyle inférieur, aryle ou alkyle inférieur substitué par aryle; R9 représente alkyle inférieur, aryle ou alkyle inférieur substitué par aryle. L'invention concerne également un procédé d'abaissement du cholestérol sérique au moyen de l'administration desdits composés seuls ou combinés à un inhibiteur de biosynthèse du cholestérol, des compositions pharmaceutiques contenant lesdits composés, ainsi qu'un procédé de préparation desdits composés.

  (Ia)式或其药学上可接受的盐，其中：Ar1和Ar2是芳基或取代R4的芳基；Ar3是芳基或取代R5的芳基；X、Y和Z是-CH2-、-CH(较低烷基)-或-C(二较低烷基)-；R和R2是-OR6、-O(CO)R6、-O(CO)OR9或-O(CO)NR6R7；R1和R3是H或较低烷基；q为0或1；r为0或1；m、n和p为0-4；前提是q和r中至少有一个为1，且m、n、p、q和r的总和为1-6；并且当p为0且r为1时，m、q和n的总和为1-5；R4选自较低烷基、R5、-CF3、-CN、-NO2和卤素；R5选自-OR6、-O(CO)R6、-O(CO)OR9、-O(CH2)1-5OR6、-O(CO)NR6R7、-NR6R7、-NR6(CO)R7、-NR6(CO)OR9、-NR6(CO)NR7R8、-NR6SO2R9、-COOR6、-CONR6R7、-COR6、-SO2NR6R7、S(O)0-2R9、-O(CH2)1-10-COOR6、-O(CH2)1-10CONR6R7、-(较低烷基)COOR6和-CH=CH-COOR6；R6、R7和R8是H、较低烷基、芳基或取代芳基的较低烷基；R9是较低烷基、芳基或取代芳基的较低烷基；还公开了通过单独或与胆固醇生物合成抑制剂组合使用来降低血清胆固醇的方法、包含它们的制药组合物以及制备它们的方法。
• Substituted beta-lactam compounds useful as hypocholesterolemic agents and processes for the preparation thereof
  申请人：SCHERING CORPORATION

  公开号：EP0524595A1

  公开（公告）日：1993-01-27

  Novel compounds of the formula wherein    A is -CH=CH-B; -C≡C-B; -(CH₂)p-X-B, wherein p is 0-2 and X is a bond, -NH- or-S(O)₀₋₂; optionally substituted heteroaryl or benzofused heteroaryl; -C(O)-B; or wherein k is 1-2;    D is B'-(CH₂)mC(O)-, wherein m is 1-5; B'-(CH₂)q-, wherein q is 2-6; B'-(CH₂)e-Z-(CH₂)r-, wherein Z is -O-, -C(O)-, phenylene, -NR₈- or -S(O)₀₋₂-, e is 0-5 and r is 1-5, provided that the sum of e and r is 1-6; B'-(alkenylene)-; B'-(alkadienylene)-; B'-(CH₂)t-Z-(alkenylene), wherein t is 0-3, provided that the sum of t and the number of carbon atoms in the alkenylene chain is 2-6; B'-(CH₂)f-V-(CH₂)g-, wherein V is cycloalkylene, f is 1-5 and g is 0-5, provided that the sum of f and g is 1-6; B'-(CH₂)t-V-(alkenylene) or B'-(alkenylene)-V-(CH₂)t-, provided that the sum of t and the number of carbon atoms in the alkenylene chain is 2-6; B'-(CH₂)a-Z-(CH₂)b-V-(CH₂)d-, wherein a, b and d are 0-6, provided that the sum of a, b and d is 0-6; T(CH₂)s-, wherein T is cycloalkyl and s is 1-6; naphthylmethyl or optionally substituted heteroarylmethyl;    B is optionally substituted phenyl;    B' is naphthyl, optionally substituted heteroaryl or optionally substituted phenyl;    R is hydrogen, fluoro, alkyl, alkenyl, alkynyl, or B-(CH₂)h-, wherein h is 0-3;    R4 is optionally substituted phenyl, indanyl, benzofuranyl, tetrahydronaphthyl, pyridyl, pyrazinyl, pyrimidinyl or quinolyl; are disclosed, as well as their use as hypocholesterolemic agents; the method of using compounds of the formula II wherein    R₂₀ is optionally substituted phenyl, optionally substituted naphthyl, optionally substituted heteroaryl, or optionally substituted benzofused heteroaryl,    R₂₁, R₂₂ and R₂₃ are independently selected from H or R₂₀;    E, F and G are independently a bond; cycloalkylene; alkylene; alkenylene; alkynylene; a substituted alkylene, alkenylene or alkynylene chain ; an interrupted alkylene, alkenylene or alkynylene chain ; or an interrupted alkylene, alkenylene or alkynylene chain substituted by one or more substituents; or one of R₂₁-E and R₂₂-F is selected from the group consisting of halogeno, OH, alkoxy, -OC(O)R₅, -NR₁₀R₁₁, -SH or -S(alkyl);    R₅ is alkyl, phenyl, R₁₄-phenyl, benzyl or R₁₄-benzyl;    R₁₀ and R₁₁ are independently selected from H and lower alkyl, or a pharmaceutically acceptable salt thereof, in a pharmaceutically aceptable carrier as hypocholesterolemic agents is also disclosed.

  式中的新型化合物 其中 A 是-CH=CH-B；-C≡C-B；-(CH₂)p-X-B，其中 p 是 0-2 和 X 是键、-NH- 或-S(O)₀₋₂；任选取代的杂芳基或苯并杂芳基；-C(O)-B；或 其中 k 为 1-2； D 是 B'-(CH₂)mC(O)-，其中 m 是 1-5； B'-(CH₂)q-，其中 q 是 2-6；B'-(CH₂)e-Z-(CH₂)r-，其中 Z 为-O-、-C(O)-、亚苯基、-NR₈- 或-S(O)₀₋₂-，e 为 0-5，r 为 1-5，条件是 e 和 r 之和为 1-6；B'-(烯烃)-； B'-(烯二烯)-； B'-(CH₂)t-Z-(烯烃)，其中 t 为 0-3，条件是 t 与烯烃链中碳原子数之和为 2-6；B'-(CH₂)f-V-(CH₂)g-，其中 V 为环亚烃，f 为 1-5，g 为 0-5，条件是 f 与 g 之和为 1-6；B'-(CH₂)t-V-(烯烃)或 B'-(烯烃)-V-(CH₂)t-，条件是 t 与烯烃链中碳原子数之和为 2-6；B'-(CH₂)a-Z-(CH₂)b-V-(CH₂)d-，其中 a、b 和 d 为 0-6，条件是 a、b 和 d 之和为 0-6；T(CH₂)s-，其中 T 为环烷基，s 为 1-6；萘甲基或任选取代的杂芳基甲基； B 是任选取代的苯基； B' 是萘基、任选取代的杂芳基或任选取代的苯基； R 是氢、氟、烷基、烯基、炔基或 B-(CH₂)h-，其中 h 是 0-3； R4 是任选取代的苯基、茚基、苯并呋喃基、四氢萘基、吡啶基、吡嗪基、嘧啶基或醌基； 的化合物，以及它们作为降胆固醇剂的用途；使用式 II 化合物的方法 其中 R₂₀ 是任选取代的苯基、任选取代的萘基、任选取代的杂芳基或任选取代的苯并杂芳基、 R₂₁、R₂₂ 和 R₂₃ 独立选自 H 或 R₂₀； E、F 和 G 独立地为键；环烷基；亚烷基；亚烯基；亚炔基；取代的亚烷基、亚烯基或亚炔基链；间断的亚烷基、亚烯基或亚炔基链；或被一个或多个取代基取代的间断亚烷基、烯基或炔基链；或 R₂₁-E 和 R₂₂-F 中的一个选自由卤素、OH、烷氧基、-OC(O)R₅、-NR₁₀R₁₁、-SH 或 -S(烷基)组成的组； R₅ 是烷基、苯基、R₁₄-苯基、苄基或 R₁₄-苄基； R₁₀ 和 R₁₁ 独立选自 H 和低级烷基，或其药学上可接受的盐，以药学上可接受的载体作为降胆固醇剂也已公开。