2-methylamino-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole | 88013-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methylamino-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole
• 英文别名: N-methyl-6-phenylimidazo[2,1-b][1,3,4]thiadiazol-2-amine
• CAS: 88013-14-3
• 化学式: C₁₁H₁₀N₄S
• 分子量: 230.293
• InChiKey: CBSSHWCJURWFFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴苯乙酮 、 2-bromo-6-phenylimidazo<2,1-b>-1,3,4-thiadiazole 、 2-氨基-5-溴-1,3,4-噻二唑 以 N-甲基乙酰胺 、 ice-water 、 乙醇 、 氯仿 、 水 为溶剂， 以12.6 g (55%)的产率得到2-methylamino-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole
  参考文献：
  名称：

  Novel hypotensive imidazothiadiazolealkenecarboxamides

  摘要：

  式子为##STR1##的咪唑噻二唑烯丙酰胺化合物，其中R.sup.1为氢、芳基、取代芳基或环烷基或脂肪烃基，该基可以被O、S、N、N-烷基、N-芳基或N-芳基烷基打断，且可以取代，R.sup.8与R.sup.1的含义相同，X代表氧、硫或基团NR.sup.9 R.sup.10，其他基团具有不同的定义，以及它们的酸加成盐，表现出降压活性。

  公开号：

  US04585873A1

文献信息

• Novel hypotensive imidazothiadiazolealkanecarboxamides
  申请人：Bayer Aktiengesellschaft

  公开号：US04657905A1

  公开（公告）日：1987-04-14

  Imidazothiadiazolealkenecarboxamides of the formula ##STR1## in which R.sup.1 is hydrogen, aryl, substituted aryl or a cyclic or aliphatic hydrocarbon radical which is optionally interrupted by O, S, N, N-alkyl, N-aryl or N-aralkyl and which is optionally substituted, R.sup.8 having the meaning indicated for R.sup.1, and X representing oxygen, sulphur or the radical NR.sup.9 R.sup.10, the other radical having various definitions, and acid addition salts thereof, exhibit hypotensive activity.

  公式为##STR1##的咪唑噻二唑烯丙酰胺化合物，其中R.sup.1为氢、芳基、取代芳基或环烷基或脂肪烃基，其可被O、S、N、N-烷基、N-芳基或N-芳烷基中断，且可被取代，R.sup.8具有R.sup.1所述的含义，X代表氧、硫或基团NR.sup.9R.sup.10，另一基团具有各种定义，以及其酸盐加合物，表现出降压活性。
• Amidazothiodiazone carbonyl compounds useful to prepare novel
  申请人：Bayer Aktiengesellschaft

  公开号：US04703125A1

  公开（公告）日：1987-10-27

  A carbonyl compound of the formula ##STR1## in which R.sup.1 denotes hydrogen, aryl, substituted aryl or a straight-chain or cyclic, saturated or unsaturated aliphatic hydrocarbon radical, which is optionally interrupted by O, S, N, N-alkyl, N-aryl or N-aralkyl, and which is optionally substituted by hydroxyl, alkoxy, alkyl, trifluoromethyl, halogen, phenyl, alkoxycarbonyl or dialkylamino, the two alkyl radicals together with the nitrogen atom optionally forming a 5 to 7-membered ring, which optionally contains a heteroatom from the group comprising O, S, NH or N-alkyl and these aforementioned alkyl and phenyl radicals in turn optionally being substituted by halogen, trifluoromethyl, alkyl, aryl, aralkyl, alkoxy, alkylmercapto or SO.sub.2 -alkyl, R.sup.2 represents the radical CXR.sup.8, R.sup.8 having the meaning indicated for R.sup.1 and being identical to or different from R.sup.1, and X representing oxygen, sulphur or the radical NR.sup.9 R.sup.10, R.sup.9 and R.sup.10 being identical or different and each having the meanings of R.sup.1 and being identical to or different from R.sup.1 ; or represents the radical SO.sub.n R.sup.11, n denoting 1 or 2 and R.sup.11 having the meaning indicated for R.sup.1 and being identical to or different from R.sup.1, or R.sup.1 and R.sup.2 together represent a group of the general formula .dbd.C(R.sup.12)(Y--R.sup.13), Y representing oxygen, sulphur, NH or N-alkyl, and R.sup.12 and R.sup.13 each having the meaning indicated for R.sup.1, being identical to or different from one another and R.sup.1, and optionally together forming, with inclusion of .dbd.C--Y, a 5 to 7-membered ring, which optionally contains a heteroatom from the group comprising O, S, NH or N-alkyl, R.sup.3 has the meaning indicated for R.sup.1 and is identical to or different from R.sup.1, or represents furyl, phenyl, thienyl, pyrimidyl, pyrazinyl, quinolinyl, isoquinolinyl or pyridyl, the rings optionally being substituted by 1, 2 or 3 identical or different substituents from the group comprising alkyl, aryl, alkoxy, halogen, nitro, trifluoromethyl, SO.sub.n -alkyl (n=0, 1 or 2) or NR.sup.9 R.sup.10, R.sup.9 and R.sup.10 having the meaning indicated above, and R.sup.4 represents hydrogen, trifluoromethyl or alkyl. These compounds are useful as intermediates in the preparation of alkene carboxamides which are useful as antihypertensives, diuretics and uricosuric agents.

  化学式为##STR1##的羰基化合物，其中R.sup.1表示氢、芳基、取代芳基或直链或环状、饱和或不饱和的脂肪族碳氢基团，该基团可以被O、S、N、N-烷基、N-芳基或N-芳基烷基所中断，且可以被羟基、烷氧基、烷基、三氟甲基、卤素、苯基、烷氧羰基或二烷基氨基取代，两个烷基与氮原子可以一起形成5到7元环，该环中可以包含来自O、S、NH或N-烷基的杂原子，这些烷基和苯基可以被卤素、三氟甲基、烷基、芳基、芳基烷基、烷氧基硫醇或SO.sub.2-烷基所取代，R.sup.2代表CXR.sup.8基团，其中R.sup.8具有R.sup.1所示的含义，与R.sup.1相同或不同，X代表氧、硫或基团NR.sup.9 R.sup.10，其中R.sup.9和R.sup.10相同或不同，且具有R.sup.1所示的含义，与R.sup.1相同或不同；或者代表SO.sub.n R.sup.11基团，n表示1或2，R.sup.11具有R.sup.1所示的含义，与R.sup.1相同或不同，或者R.sup.1和R.sup.2一起代表.dbd.C(R.sup.12)(Y--R.sup.13)基团，其中Y代表氧、硫、NH或N-烷基，R.sup.12和R.sup.13具有R.sup.1所示的含义，相同或不同于彼此和R.sup.1，且可以一起形成包括.dbd.C--Y的5到7元环，该环可以包含来自O、S、NH或N-烷基的杂原子，R.sup.3具有R.sup.1所示的含义，与R.sup.1相同或不同，或者代表呋喃基、苯基、噻吩基、嘧啶基、吡嗪基、喹啉基、异喹啉基或吡啶基，环可以被1、2或3个相同或不同的取代基所取代，这些取代基来自烷基、芳基、烷氧基、卤素、硝基、三氟甲基、SO.sub.n-烷基(n=0、1或2)或NR.sup.9 R.sup.10，其中R.sup.9和R.sup.10具有上述所示的含义，R.sup.4代表氢、三氟甲基或烷基。这些化合物在烯烃羧酰胺的制备中是有用的，这些烯烃羧酰胺在抗高血压、利尿和尿酸排泄剂中是有用的。
• Imidazothiadiazolealkylene carboxylic acids
  申请人：Bayer Aktiengesellschaft

  公开号：US04709031A1

  公开（公告）日：1987-11-24

  An alkenecarboxylic acid of the formula ##STR1## in which R.sup.1 denotes hydrogen, aryl, substituted aryl or a straight-chain or cyclic, saturated or unsaturated aliphatic hydrocarbon radical, which is optionally interrupted by O, S, N, N-alkyl, N-aryl or N-aralkyl, and which is optionally substituted by hydroxyl, alkoxy, alkyl, trifluoromethyl, halogen, phenyl, alkoxycarbonyl or dialkylamino, the two alkyl radicals together with the nitrogen atom optionally forming a 5 to 7-membered ring, which optionally contains a heteroatom from the group comprising O, S, NH or N-alkyl and these aforementioned alkyl and phenyl radicals in turn optionally being substituted by halogen, trifluoromethyl, alkyl, aryl, aralkyl, alkoxy, alkylmercapto or SO.sub.2 -alkyl, R.sup.2 represents the radical CXR.sup.8, R.sup.8 having the meaning indicated for R.sup.1 and being identical to or different from R.sup.1, and X representing oxygen, sulphur or the radical NR.sup.9 R.sup.10, R.sup.9 and R.sup.10 being identical or different and each having the meanings of R.sup.1 and being identical to or different from R.sup.1 ; or represents the radical SO.sub.n R.sup.11, n denoting 1 or 2 and R.sup.11 having the meaning indicated for R.sup.1 and being identical to or different from R.sup.1, or R.sup.1 and R.sup.2 together represents a group of the general formula .dbd.C(R.sup.12)(Y--R.sup.13), Y representing oxygen, sulphur, NH or N-alkyl, and R.sup.12 and R.sup.13 each having the meaning indicated for R.sup.1, being identical to or different from one another and R.sup.1, and optionally together forming, with inclusion of .dbd.C--Y, a 5 to 7-membered ring, which optionally contains a heteroatom from the group comprising O, S, NH or N-alkyl, R.sup.3 has the meaning indicated for R.sup.1 and is identical to or different from R.sup.1, or represents furyl, phenyl, thienyl, pyrimidyl, pyrazinyl, quinolinyl, isoquinolinyl or pyridyl, the rings optionally being substituted by 1, 2 or 3 identical or different substituents from the group comprising alkyl, aryl, alkoxy, halogen, nitro, trifluoromethyl, SO.sub.n -alkyl (n=0, 1 or 2) or NR.sup.9 R.sup.10, R.sup.9 and R.sup.10 having the meaning indicated above, R.sup.4 represents hydrogen, trifluoromethyl or alkyl, and R.sup.5 represents hydrogen, alkyl, cyano, halogen, nitro, SO.sub.n -alkyl (n=0, 1 or 2) or CXR.sup.8. These alkene carboxylic acids can be reacted with amine of the formula HNR.sup.6 R.sup.7 to give amides which are useful as antihypertnsives, diuretics and uricosuric agents.

  该公式中的烯丙基羧酸为##STR1##其中R.sup.1代表氢、芳基、取代芳基或直链或环状、饱和或不饱和的脂肪烃基，其中可由O、S、N、N-烷基、N-芳基或N-芳基烷基中断，且可由羟基、烷氧基、烷基、三氟甲基、卤素、苯基、烷氧羰基或二烷基氨基取代，两个烷基与氮原子可选地形成5至7个成员环，其中可包含来自O、S、NH或N-烷基的杂原子，这些上述的烷基和苯基基团反过来可选地由卤素、三氟甲基、烷基、芳基、芳基烷基、烷氧基、烷基硫醇或SO.sub.2-烷基取代，R.sup.2代表基团CXR.sup.8，其中R.sup.8具有上述R.sup.1所示的含义，且与R.sup.1相同或不同，X代表氧、硫或基团NR.sup.9 R.sup.10，其中R.sup.9和R.sup.10相同或不同，每个具有R.sup.1所示的含义，并且与R.sup.1相同或不同;或代表基团SO.sub.n R.sup.11，n表示1或2，R.sup.11具有上述R.sup.1所示的含义，且与R.sup.1相同或不同，或R.sup.1和R.sup.2一起代表具有.dbd.C(R.sup.12)(Y--R.sup.13)的一般式的基团，其中Y代表氧、硫、NH或N-烷基，R.sup.12和R.sup.13各自具有上述R.sup.1所示的含义，相同或不同，并且与R.sup.1相同或不同;并且可选择地与.dbd.C--Y一起形成包括O、S、NH或N-烷基的杂原子的5至7个成员环，R.sup.3具有上述R.sup.1所示的含义，与R.sup.1相同或不同，或代表呋喃基、苯基、噻吩基、嘧啶基、吡嗪基、喹啉基、异喹啉基或吡啶基，环可选择地由1、2或3个相同或不同的取代基团从包括烷基、芳基、烷氧基、卤素、硝基、三氟甲基、SO.sub.n-烷基(n=0,1或2)或NR.sup.9 R.sup.10的群中取代，其中R.sup.9和R.sup.10具有上述所示的含义，R.sup.4代表氢、三氟甲基或烷基，R.sup.5代表氢、烷基、氰基、卤素、硝基、SO.sub.n-烷基(n=0,1或2)或基团CXR.sup.8。这些烯丙基羧酸可以与式为HNR.sup.6 R.sup.7的胺反应，产生有用的抗高血压、利尿和尿酸排泄剂的酰胺。
• Imidazothiadiazolalkencarbonsäureamide, neue Zwischenprodukte zu ihrer Herstellung, ihre Herstellung und ihre Verwendung in Arzneimitteln
  申请人：BAYER AG

  公开号：EP0088323B1

  公开（公告）日：1987-05-06
• US4585873A
  申请人：——

  公开号：US4585873A

  公开（公告）日：1986-04-29