2-methyl-3-oxo-4,5,6,7-tetrahydro-(2H)-1,2-benzisothiazole 1,1-dioxide | 1135949-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-methyl-3-oxo-4,5,6,7-tetrahydro-(2H)-1,2-benzisothiazole 1,1-dioxide
• 英文别名: N-methyltetrahydrosaccharin；2-methyltetrahydrosaccharin；2-methyl-1,1-dioxo-4,5,6,7-tetrahydro-1,2-benzothiazol-3-one
• CAS: 1135949-47-1
• 化学式: C₈H₁₁NO₃S
• 分子量: 201.246
• InChiKey: LOWIDJBPWUJAJT-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  353.3±25.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 2-methyl-3-oxo-4,5,6,7-tetrahydro-(2H)-1,2-benzisothiazole 1,1-dioxide 以 乙醚 为溶剂， 以96%的产率得到2-methyl-3-oxo-4,5,6,7-tetrahydro-(2H)-1,2-benzisothiazolo[4,5-c]pyrazoline 1,1-dioxide
  参考文献：
  名称：

  4,5-二烷基取代的3-氧代-（2H）-异噻唑1,1-二氧化物与重氮甲烷的反应

  摘要：

  It has been established that the interaction of diazomethane with 4,5-dialkyl-substituted 3-oxo-(2H)-isothiazole 1,1-dioxides proceeds in two stages. Initially alkylation of the sulfonimide nitrogen atom and the carbonyl group oxygen atom occurs (in a ratio of similar to 3:2), then there is a regioselective cycloaddition of diazomethane at the C=C double bond with the formation of the corresponding N-methyloxoisothiazolopyrazolines and 3-methoxyisothiazolopyrazolines.

  DOI：

  10.1007/s10593-008-0065-x
• 作为产物：
  描述：

  4,5,6,7-四氢-1,2-苯并异噻唑-3(2H)-酮 1,1-二氧化物 、 对甲砜基甲苯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以51%的产率得到2-methyl-3-oxo-4,5,6,7-tetrahydro-(2H)-1,2-benzisothiazole 1,1-dioxide
  参考文献：
  名称：

  4,5-二烷基取代的3-氧代-（2H）-异噻唑1,1-二氧化物与重氮甲烷的反应

  摘要：

  It has been established that the interaction of diazomethane with 4,5-dialkyl-substituted 3-oxo-(2H)-isothiazole 1,1-dioxides proceeds in two stages. Initially alkylation of the sulfonimide nitrogen atom and the carbonyl group oxygen atom occurs (in a ratio of similar to 3:2), then there is a regioselective cycloaddition of diazomethane at the C=C double bond with the formation of the corresponding N-methyloxoisothiazolopyrazolines and 3-methoxyisothiazolopyrazolines.

  DOI：

  10.1007/s10593-008-0065-x

文献信息

• Novel 2-saccharinylmethyl and 4,5,6,7-tetrahydro-2-saccharinylmethyl phosphates, phosphonates and phosphinates useful as proteolytic enzyme inhibitors and compositions and method of use thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0549073A1

  公开（公告）日：1993-06-30

  Novel 4-R₁-R₂-R₃-2-saccharinylmethyl, 4-R₄-4-R₅-6-R₆-4,5,6,7-tetrahydro-2-saccharinylmethyl and 4,7-C-4,5,6,7-tetrahydro-2-saccharinylmethyl phosphates, phosphonates and phosphinates of formulas I, II and IIA respectively are useful in the treatment of degenerative diseases, and compositions containing them, methods for using them to treat degenerative diseases, and processes for their preparation by reaction of the corresponding 2-halomethylsaccharins with a phosphate, phosphonate or phosphinic acidderivative.

  分别为式 I、II 和 IIA 的新型 4-R₁-R₂-R₃-2-糖精基甲基、4-R₄-4-R₅-6-R₆-4,5,6,7-四氢-2-糖精基甲基和 4,7-C-4,5,6,7-四氢-2-糖精基甲基膦酸盐、膦酸盐和膦酸盐 可用于治疗退行性疾病，以及含有这些物质的组合物、使用这些物质治疗退行性疾病的方法，以及通过相应的 2-半甲基糖与磷酸盐、膦酸盐或膦酸衍生物反应制备这些物质的工艺。
• 2-Saccharinylmethyl heterocyclic carboxylates useful as proteolytic enzyme inhibitors and pharmaceutical compositions containing them
  申请人：STERLING WINTHROP INC.

  公开号：EP0550111A1

  公开（公告）日：1993-07-07

  4-R⁴-R⁵-2-Saccharinylmethyl heterocyclic carboxylates, having the formula: wherein:    Het is a 5- or 6-membered monocyclic heterocycle or a 9- or 10-membered bicyclic heterocycle containing from 1 to 2 heteroatoms selected from oxygen, nitrogen and sulfur or said heterocycles substituted by from one to three, the same or different, members of the group consisting of lower-alkyl, perfluorolower-alkyl, lower-alkoxy, oxo, phenyl, halogen, and -O-(C₂-C₁₀ alkylene)-N=B where N=B is dilower-alkylamino, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1-piperazinyl, or 4-lower-alkyl-1-piperazinyl;    R⁴ is hydrogen, halogen , lower-alkyl, perfluorolower-alkyl, perchlorolower-alkyl, lower-alkenyl, lower-alkynyl, cyano, carboxamido, amino, lower-alkylamino, dilower-alkylamino, lower-alkoxy, benzyloxy, lower-alkoxycarbonyl, hydroxy or phenyl; and    R⁵ is hydrogen or from one to two substituents in any of the 5-, 6- or 7-positions. The compounds of the present invention inhibit the activity of serine proteases, specifically human leukocyte elastase and the chymotrypsin-like enzymes, and are thus useful in the treatment of degenerative disease conditions such as emohysema, rheumatoid arthritis, pancreatitis, cystic fibrosis, chronic bronchitis, adult respiratory distress syndrome, inflammatory bowel disease, psoriasis, bullous pemphigoid and alpha-1-antitrypsin deficiency.

  4-R⁴-R⁵-2-糖精甲基杂环羧酸盐，其化学式为 其中 Het 是 5 或 6 元单环杂环或 9 或 10 元双环杂环，其中含有 1 至 2 个选自氧、氮和硫的杂原子，或所述杂环被 1 至 3 个相同或不同的杂原子取代、由低级烷基、全氟低级烷基、低级烷氧基、氧代、苯基、卤素和-O-(C₂-C₁₀亚烷基)-N=B 组成的组中的成员，其中 N=B 是稀低级烷基氨基、1-吡咯烷基、1-哌啶基、4-吗啉基、1-哌嗪基或 4-低级烷基-1-哌嗪基； R⁴ 是氢、卤素、低级烷基、全氟低级烷基、全氯低级烷基、低级烯基、低级炔基、氰基、羧酰胺基、氨基、低级烷基氨基、稀释低级烷基氨基、低级烷氧基、苄氧基、低级烷氧基羰基、羟基或苯基；以及 R⁵ 是氢或 5、6 或 7 位上的一至两个取代基。 本发明的化合物可抑制丝氨酸蛋白酶的活性，特别是人白细胞弹性蛋白酶和糜蛋白酶样酶，因此可用于治疗退行性疾病，如肺气肿、类风湿性关节炎、胰腺炎、囊性纤维化、慢性支气管炎、成人呼吸窘迫综合征、炎症性肠病、银屑病、大疱性类天疱疮和α-1-抗胰蛋白酶缺乏症。
• Novel, 2-saccharinylmethyl phosphates, phosphonates and phosphinates useful as proteolytic enzyme inhibitors and compositions and method of use thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0601623A1

  公开（公告）日：1994-06-15

  Novel 4-R₁-R₂-R₃-2-saccharinylmethyl phosphates, phosphonates and phosphinates of formula I herein, useful in the treatment of degenerative diseases, and compositions containing them are described, together with methods for using them to treat degenerative diseases, and processes for their preparation by reaction of the corresponding 2-halomethylsaccharins with a phosphate, phosphonate or phosphinic acid of formula III herein in the presence of an acid-acceptor.

  本发明描述了可用于治疗退行性疾病的式 I 的新型 4-R₁-R₂-R₃-2-糖基甲基磷酸酯、膦酸盐和膦酸盐以及含有它们的组合物，同时还描述了使用它们治疗退行性疾病的方法，以及在酸受体存在下通过相应的 2-卤代甲基糖与式 III 的磷酸、膦酸盐或膦酸反应制备它们的工艺。
• SUBSTITUTED 2-(PHOSPHINYLOXYMETHYL)-1,2,5-THIADIAZOLIDIN-3-ONE 1,1-DIOXIDES AND COMPOSITIONS AND METHOD OF USE THEREOF
  申请人：SANOFI WINTHROP, INC.

  公开号：EP0794956A1

  公开（公告）日：1997-09-17
• EP0794956A4
  申请人：——

  公开号：EP0794956A4

  公开（公告）日：1998-02-11