SM-10661 | 119384-34-8

• 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: SM-10661
• 英文别名: 3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one；3,5-dimethyl-2-(pyridin-3-yl)thiazolidin-4-one；3,5-dimethyl-2-pyridin-3-yl-1,3-thiazolidin-4-one
• CAS: 119384-34-8
• 化学式: C₁₀H₁₂N₂OS
• 分子量: 208.284
• InChiKey: FZXAQGVGSAANBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  SM-10661 、 碘甲烷 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以39%的产率得到5,5,3-trimethyl-2-(pyridin-3-yl)-thiazolidin-4-one
  参考文献：
  名称：

  Certain pyridyl-thiazolidin-4-one having anti-ulcer activity

  摘要：

  一种由以下式表示的2-吡啶基噻唑啉-4-酮衍生物：其中R.sub.1和R.sub.2分别为氢原子、C.sub.1-C.sub.20烷基、C.sub.2-C.sub.20烯基、C.sub.2-C.sub.20炔基、芳基、C.sub.3-C.sub.8环烷基或可能具有取代基的芳基烷基，R.sub.3为氢原子、C.sub.1-C.sub.20烷基、C.sub.2-C.sub.20烯基、C.sub.2-C.sub.20炔基、C.sub.3-C.sub.8环烷基或可能具有取代基的芳基烷基，P为吡啶基或其可能具有取代基的N-取代吡啶盐基，所述取代基选自卤原子、氰基、羟基、氨基、低烷基、低烷氧基、低烷基氨基、卤代低烷基、酰基、酰氧基、硫代酰基、酰胺基、羧基、低烷氧羰基、氨基甲酰基、低烷基取代的氨基甲酰基、杂环基和低环烷基，n表示0、1或2的整数，或其药学上可接受的盐，以及作为有效成分的抗溃疡药物，包含上述2-吡啶基噻唑啉-4-酮衍生物或其药学上可接受的盐。

  公开号：

  US05021435A1
• 作为产物：
  描述：

  3-吡啶甲醛 、 (+)-thiolactic acid 、 甲胺 以 甲苯 为溶剂， 以68%的产率得到SM-10661
  参考文献：
  名称：

  Certain pyridyl-thiazolidin-4-one having anti-ulcer activity

  摘要：

  一种由以下式表示的2-吡啶基噻唑啉-4-酮衍生物：其中R.sub.1和R.sub.2分别为氢原子、C.sub.1-C.sub.20烷基、C.sub.2-C.sub.20烯基、C.sub.2-C.sub.20炔基、芳基、C.sub.3-C.sub.8环烷基或可能具有取代基的芳基烷基，R.sub.3为氢原子、C.sub.1-C.sub.20烷基、C.sub.2-C.sub.20烯基、C.sub.2-C.sub.20炔基、C.sub.3-C.sub.8环烷基或可能具有取代基的芳基烷基，P为吡啶基或其可能具有取代基的N-取代吡啶盐基，所述取代基选自卤原子、氰基、羟基、氨基、低烷基、低烷氧基、低烷基氨基、卤代低烷基、酰基、酰氧基、硫代酰基、酰胺基、羧基、低烷氧羰基、氨基甲酰基、低烷基取代的氨基甲酰基、杂环基和低环烷基，n表示0、1或2的整数，或其药学上可接受的盐，以及作为有效成分的抗溃疡药物，包含上述2-吡啶基噻唑啉-4-酮衍生物或其药学上可接受的盐。

  公开号：

  US05021435A1

文献信息

• Certain pyridyl-thiazolidin-4-one having anti-ulcer activity
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US05021435A1

  公开（公告）日：1991-06-04

  A 2-pyridyl-thiazolidin-4-one derivative represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each a hydrogen atom, an C.sub.1 -C.sub.20 alkyl group, an C.sub.2 -C.sub.20 alkenyl group, an C.sub.2 -C.sub.20 alkynyl group, an aryl group, a C.sub.3 -C.sub.8 cycloalkyl group or an aralkyl group which may have a substituent, R.sub.3 is a hydrogen atom, an C.sub.1 -C.sub.20 alkyl group, an C.sub.2 -C.sub.20 alkenyl group, an C.sub.2 -C.sub.20 alkynyl group, a C.sub.3 -C.sub.8 cycloalkyl group or an aralkyl group which may have a substituent, P is a pyridyl group or its N-substituted pyridinium salt which may have a substituent, said substituent being selected from the group consisting of halogen atom, cyano group, hydroxy group, amino group, lower alkyl group, lower alkoxy group, lower alkylamino group, halogenated lower alkyl group, acyl group, acyloxy group, acylthio group, acylamino group, carboxyl group, lower alkoxycarbonyl group, carbamoyl group, lower alkyl substituted carbamoyl group, heterocyclic group, and lower cycloalkyl group, and n represents an integer of 0, 1 or 2, or a pharmaceutically acceptable salts thereof and an anti-ulcer agent which contains, as an effective ingredient, said 2-pyridyl-thiazolidine-4-one derivative or a pharmaceutically acceptable salt thereof.

  一种由以下式表示的2-吡啶基噻唑啉-4-酮衍生物：其中R.sub.1和R.sub.2分别为氢原子、C.sub.1-C.sub.20烷基、C.sub.2-C.sub.20烯基、C.sub.2-C.sub.20炔基、芳基、C.sub.3-C.sub.8环烷基或可能具有取代基的芳基烷基，R.sub.3为氢原子、C.sub.1-C.sub.20烷基、C.sub.2-C.sub.20烯基、C.sub.2-C.sub.20炔基、C.sub.3-C.sub.8环烷基或可能具有取代基的芳基烷基，P为吡啶基或其可能具有取代基的N-取代吡啶盐基，所述取代基选自卤原子、氰基、羟基、氨基、低烷基、低烷氧基、低烷基氨基、卤代低烷基、酰基、酰氧基、硫代酰基、酰胺基、羧基、低烷氧羰基、氨基甲酰基、低烷基取代的氨基甲酰基、杂环基和低环烷基，n表示0、1或2的整数，或其药学上可接受的盐，以及作为有效成分的抗溃疡药物，包含上述2-吡啶基噻唑啉-4-酮衍生物或其药学上可接受的盐。
• Direct Enantiomeric Separation of Platelet-activating Factor Receptor Antagonist SM-10661 by Ligand-exchange High-performance Liquid Chromatography with a Copper(II)<i>N,S</i>-Dioctyl-<scp>D</scp>-penicillamine Complex
  作者：Masahiko Okamoto、Youichi Ueda、Ken-ichi Takahashi、Hiroshi Nakazawa、Tadashi Doi

  DOI：10.1271/bbb.59.1740

  日期：1995.1

  The enantiomeric separation of SM-10661, a platelet activating factor receptor antagonist, was investigated by HPLC using ligand-exchange chiral stationary phases. The stereoisomers of SM-10661 could all be separated by ligand-exchange HPLC with a Cu(II) N, S-dioctyl-D-penicillamine complex (Sumichiral OA-5000). The mechanism for the resolution includes the involvement of hydrophobic interactions between SM-10661 and Cu(II) D-penicillamine.

  使用配体交换手性固定相，通过 HPLC 研究血小板活化因子受体拮抗剂 SM-10661 对映体的分离。 SM-10661 的立体异构体均可通过配体交换 HPLC 使用 Cu(II) N,S-二辛基-D-青霉胺复合物 (Sumichiral OA-5000) 进行分离。拆分机制包括 SM-10661 和 Cu(II) D-青霉胺之间的疏水相互作用。
• Thiazolidin-4-one derivatives and acid addition salts thereof useful for
  申请人：Sumitomo Chemical Company, Limited

  公开号：US05106860A1

  公开（公告）日：1992-04-21

  Thiazolidin-4-one derivative represented by the following general formula (I) and acid addition salts thereof ##STR1## wherein; R.sup.1 and R.sup.2 are the same or different and denote each (i) a residue represented by the general formula --A--R.sup.4 wherein, A denotes a single bond, C.sub.1 -C.sub.8 alkylene, C.sub.2 -C.sub.8 alkenylene, or C.sub.2 -C.sub.8 alkynylene and R.sup.4 denotes hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, or C.sub.1 -C.sub.6 haloalkyl,or (ii) a residue represented by the general formula ##STR2## wherein, B denotes a single bond or C.sub.1 -C.sub.6 alkylene, R.sup.5 denotes hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, substituted silyl, or substituted or unsubstituted aryl, n and n' denote each an integer of 2 to 4, m denotes an integer of 1 to 3, and m' denotes an integer of 0 to 2; R.sup.3 denotes hydrogen, C.sub.1 -C.sub.2 alkyl, allyl, 2-propynyl, or (c) the general formula --F--R.sup.9 wherein, F denotes C.sub.2 -C.sub.6 alkylene and R.sup.9 denotes a nitrogen-containing heterocyclic aromatic residue or an amino group represented by the general formula ##STR3## (R.sup.10 denotes hydrogen, C.sub.2 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkanoyl and R.sup.11 denotes hydrogen or C.sub.1 -C.sub.4 alkyl or R.sup.10 in combination with R.sup.11 denotes a 5- to 7-membered cyclic amino group which optionally contains other hetero atoms. Having selective PAF-antagonistic activities, these compounds are very useful as preventive and curative agents for PAF-induced diseases, for example, various kinds of inflammation, allergic diseases, circulatory diseases, and gastro-intestinal diseases.

  以下是由下列一般式（I）表示的噻唑烷-4-酮衍生物及其酸加成盐：##STR1## 其中，R.sup.1和R.sup.2相同或不同，分别表示（i）由一般式--A--R.sup.4表示的残基，其中，A表示单键，C.sub.1-C.sub.8烷基，C.sub.2-C.sub.8烯基或C.sub.2-C.sub.8炔基，而R.sup.4表示氢，C.sub.1-C.sub.12烷基，C.sub.2-C.sub.8烯基，C.sub.3-C.sub.8环烷基或C.sub.1-C.sub.6卤代烷基；或（ii）由下列一般式表示的残基：##STR2## 其中，B表示单键或C.sub.1-C.sub.6烷基，R.sup.5表示氢，C.sub.1-C.sub.6烷基，C.sub.2-C.sub.8烯基，C.sub.3-C.sub.8环烷基，取代硅烷基或取代或未取代芳基，n和n'分别表示2到4的整数，m表示1到3的整数，而m'表示0到2的整数；R.sup.3表示氢，C.sub.1-C.sub.2烷基，烯丙基，2-丙炔基或由下列一般式表示的残基--F--R.sup.9，其中，F表示C.sub.2-C.sub.6烷基，而R.sup.9表示含氮杂环芳基残基或由下列一般式表示的氨基：##STR3## （其中，R.sup.10表示氢，C.sub.2-C.sub.4烷基或C.sub.1-C.sub.4酰基，而R.sup.11表示氢或C.sub.1-C.sub.4烷基，或R.sup.10与R.sup.11组合表示可选地含有其他杂原子的5-至7-成员环氨基。）这些化合物具有选择性的PAF-拮抗活性，非常有用作为预防和治疗PAF引起的疾病，例如各种炎症，过敏性疾病，循环系统疾病和胃肠疾病的药物。
• 2-Pyridyl thiazolidin-4-one derivatives as anti-ulcer agents
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0325496A1

  公开（公告）日：1989-07-26

  A 2-pyridyl-thiazolidin-4-one derivative represented by the formula: wherein Ri and R2 are each a hydrogen atom, a C1-C20 alkyl group, a C2-C2o alkenyl group, a C2-C20 alkynyl group, an aryl group, a C3-C8 cycloalkyl group or an aralkyl group which may have a substituent, Rs is a hydrogen atom, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C2o alkynyl group, a C3-C8 cycloalkyl group or an aralkyl group which may have a substituent, P is a pyridyl group or its N-substituted pyridinium salt which may have a substituent, said substituent being selected from the group consisting of halogen atom, cyano group, hydroxy group, amino group, lower alkyl group, lower alkoxy group, lower alkylamino group, halogenated lower alkyl group, acyl group, acyloxy group, acylthio group, acylamino group, carboxyl group, lower alkoxycarbonyl group, carbamoyl group, lower alkyl substituted carbamoyl group, heterocyclic group, and lower cycloalkyl group, and n represents an integer of 0, 1 or 2, or a pharmaceutically acceptable salt thereof is an anti-ulcer agent effective against stress induced ulcers. Some of these compounds are novel.

  一种2-吡啶基噻唑烷-4-酮衍生物，由式表示： 其中 Ri 和 R2 各为氢原子、C1-C20 烷基、C2-C2o 烯基、C2-C20 炔基、芳基、C3-C8 环烷基或可带有取代基的芳烷基，Rs 为氢原子、C1-C20 烷基、C2-C20 烯基、C2-C2o 炔基、C3-C8 环烷基或可带有取代基的芳烷基、C2-C2o 烷基、C3-C8 环烷基或可带有取代基的芳基，P 是吡啶基或其 N-取代的吡啶鎓盐，可带有取代基，所述取代基可选 自卤素原子组成的组、氰基、羟基、氨基、低级烷基、低级烷氧基、低级烷基氨基、卤代低级烷基、酰基、酰氧基、酰硫基、酰氨基、羧基、低级烷氧基羰基、氨基甲酰基、低级烷基取代的氨基甲酰基、杂环基和低级环烷基，且 n 代表 0、1 或 2 的整数，或其药学上可接受的盐。其中一些化合物是新型的。
• CYP2A6 GENE JUDGMENT METHODS
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP1182266A1

  公开（公告）日：2002-02-27

  There are provided a method of determining a genotype of CYP2A6 gene on the basis of a difference in gene structures of a wild-type gene of CYP2A6 and at least one kind of mutant-type gene associated with mutation of CYP2A6 gene; the method mentioned above, wherein one kind of mutant-type gene associated with mutation of CYP2A6 gene is used, and the mutant-type gene is conversion-type CYP2A6 gene comprising the nucleotide sequence of SEQ ID NO: 4; the method mentioned above, wherein homozygous deletion and heterozygous deletion of CYP2A6 gene are determined by using at least two kinds of mutant-type genes associated with mutation of CYP2A6 gene; a method of determining a genotype of a CYP gene, characterized by carrying out a method comprising the method mentioned above to determine the genotype of the CYP gene; a diagnostic kit for determining a genotype of CYP2A6 gene, comprising 5'-primer capable of hybridizing to both exon 8 of CYP2A6 gene and exon 8 of CYP2A7 gene, 3'-primer capable of specifically hybridizing to exon 9 of CYP2A6 gene, AccII or an isoschizomer thereof, and Eco81I or an isoschizomer thereof; and the like.

  提供了一种根据CYP2A6野生型基因和至少一种与CYP2A6基因突变相关的突变型基因的基因结构差异来确定CYP2A6基因基因型的方法；上述方法中，使用一种与CYP2A6基因突变相关的突变型基因，该突变型基因为转换型CYP2A6基因，该转换型CYP2A6基因包括SEQ ID NO.4的核苷酸序列；上述方法中，使用至少两种与CYP2A6基因突变相关的突变型基因来确定CYP2A6基因的同型缺失和异型缺失；上述方法中，使用至少两种与CYP2A6基因突变相关的突变型基因来确定CYP2A6基因的同型缺失和异型缺失：4； 上述方法中，通过使用至少两种与 CYP2A6 基因突变相关的突变型基因来确定 CYP2A6 基因的同型缺失和杂合型缺失； 一种确定 CYP 基因基因型的方法，其特征在于实施包括上述方法在内的方法来确定 CYP 基因的基因型；一种确定 CYP2A6 基因基因型的诊断试剂盒，包括能与 CYP2A6 基因第 8 外显子和 CYP2A7 基因第 8 外显子杂交的 5'引物、能与 CYP2A6 基因第 9 外显子特异性杂交的 3'引物、AccII 或其异构体和 Eco81I 或其异构体；以及类似试剂。