Title:
PROCESS FOR PREPARATION OF ASYMMETRICAL BIS(THIOSEMICARBAZONES)
Document Type and Number:
Japanese Patent JP2015134798
Kind Code:
A
Abstract:
PROBLEM TO BE SOLVED: To provide a method of making asymmetrical bis(thiosemicarbazones), compounds useful as synthetic intermediates in the method, new bis(thiosemicarbazones) that can be readily accessed by use of the method, and methods of treatment and imaging utilizing some of the new bis(thiosemicarbazones).SOLUTION: The invention provides asymmetrical bis(thiosemicarbazone) compounds represented by the formula (I), a method of making the same including reaction with a primary amine of NH2R4, and methods of treatment and imaging utilizing the same (e.g., diagnostic contrast agents in the field of radioactive copper pharmaceuticals).
Inventors:
PAUL STEPHEN DONNELLY
BRETT MICHAEL PATERSON
BRETT MICHAEL PATERSON
Application Number:
JP2015043736A
Publication Date:
July 27, 2015
Filing Date:
March 05, 2015
Export Citation:
Assignee:
UNIV MELBOURNE
International Classes:
C07C337/08; A61K31/17; A61K31/18; A61K31/195; A61K31/22; A61K31/255; A61K31/30; A61K31/4015; A61K31/47; A61K31/495; A61K31/5375; A61K31/662; A61K31/69; A61K38/00; A61K38/08; A61K51/00; A61P35/00; C07D207/452; C07D215/38; C07D295/12; C07F1/08; C07F5/02; C07K7/06
Domestic Patent References:
| JP2012511513A | 2012-05-24 | |||
| JPS5946264A | 1984-03-15 | |||
| JPS59193833A | 1984-11-02 | |||
| JPH08245425A | 1996-09-24 | |||
| JPH10101566A | 1998-04-21 | |||
| JPH0772571A | 1995-03-17 |
Foreign References:
| WO2007003944A2 | 2007-01-11 | |||
| WO2008061306A1 | 2008-05-29 |
Other References:
JPN6014001977; 'Ｆｕｎｃｔｉｏｎａｌｉｚｅｄ Ｂｉｓ（ｔｈｉｏｓｅｍｉｃａｒｂａｚｏｎａｔｏ）Ｃｏｍｐｌｅｘｅｓ ｏ' Ｉｎｏｒｇ．Ｃｈｅｍ． ４６, 2007, ４６５-４８５
JPN6014001979; 'Ｍｉｘｅｄ Ｂｉｓ（ｔｈｉｏｓｅｍｉｃａｒｂａｚｏｎｅ） Ｌｉｇａｎｄｓ ｆｏｒ ｔｈｅ Ｐｒｅｐａ' Ｊ．Ｍｅｄ．Ｃｈｅｍ． ４０, 1997, １３２-１３６
JPN6015047626; Ｌｉｌｙ Ｊ． Ａｃｋｅｒｍａｎ， Ｄｏｕｇｌａｓ Ｘ． Ｗｅｓｔ， Ｃａｒｌａ Ｊ． Ｍａｔｈｉａｓ ａｎｄ Ｍａｒｋ Ａ． Ｇｒｅｅｎ: 'Ｓｙｎｔｈｅｓｉｓ ａｎｄ Ｅｖａｌｕａｔｉｏｎ ｏｆ Ｃｏｐｐｅｒ Ｒａｄｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ ｗｉｔｈ Ｍｉｘｅｄ Ｂｉｓ（ｔｈｏｓｅｍｉｃａｒｂａｚｏｎｅ） Ｌｉｇａｎｄｓ' Ｎｕｃｌｅａｒ Ｍｅｄｉｃｉｎｅ ＆ Ｂｉｏｌｏｇｙ ２６, 1999, ５５１-５５４
JPN6015047628; Ｊａｓｏｎ Ｐ． Ｈｏｌｌａｎｄ， Ｐｅｔｅｒ Ｊ． Ｂａｒｎａｒｄ， Ｓｉｍｏｎ Ｒ． Ｂａｙｌｙ，Ｈｅｌｅｎ Ｍ． Ｂｅｔｔｓ， Ｇｒａｎｔ Ｃ． Ｃｈｕｒｃｈｉｌｌ， Ｊｏｎａｔｈａｎ Ｒ． Ｄ: 'Ｓｙｎｔｈｅｓｉｓ， Ｒａｄｉｏｌａｂｅｌｌｉｎｇ ａｎｄ Ｃｏｎｆｏｃａｌ Ｆｌｕｏｒｅｓｃｅｎｃｅ Ｍｉｃｒｏｓｃｏｐｙ ｏｆ Ｓｔｙｒｅｎｅ-Ｄｅｒｉｖａｔｉｓｅｄ Ｂｉｓ（ｔｈｉｏｓｅｍｉｃａ' Ｅｕｒｏｐｅａｎ Ｊｏｕｒｎａｌ ｏｆ Ｉｎｏｒｇａｎｉｃ Ｃｈｅｍｉｓｔｒｙ １２, 2008, １９８５-１９９&
JPN6015047629; Ｄ．Ｗ． ＭｃＰｈｅｒｓｏｎ， Ｇ．Ｕｍｂｒｉｃｈｔ， ａｎｄ Ｆ． Ｆ． Ｋｎａｐｐ， Ｊｒ．: 'Ｒａｄｉｏｌａｂｅｌｌｉｎｇ ｏｆ Ｐｒｏｔｅｉｎｓ ｗｉｔｈ Ｒａｄｉｏｉｓｏｔｏｐｅｓ ｏｆ Ｃｏｐｐｅｒ ｕｓｉｎｇ ｐ-Ｃａｒｂｏｘｙａｌｋｙｌｐｈｅｎｙｌｇｌｙｏｘａｌ ｂｉｓ-（４Ｎ-Ｍｅ' Ｊｏｕｒｎａｌ ｏｆ Ｌａｂｅｌｌｅｄ Ｃｏｍｐｏｕｎｄｓ ａｎｄ Ｒａｄｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ ２８（８）, 1990, ８７７-８９９
JPN6015047631; Ｅｕｇｅｎｅ Ａ． Ｃｏａｔｓ， Ｓｔａｎｌｅｙ Ｒ． Ｍｉｌｓｔｅｉｎ， Ｍｉｃｈａｅｌ Ａ． Ｐｌｅｉｓｓ， ａｎｄ Ｊｅｆｆｒｅｙ Ａ． Ｒｏｅｓｅｎｅｒ: 'Ｃｏｍｐａｒａｔｉｖｅ Ａｎａｌｙｓｉｓ ｏｆ ｔｈｅ Ｃｙｔｏｔｏｘｉｃｉｔｙ ｏｆ Ｓｕｂｓｔｉｔｕｔｅｄ ［Ｐｈｅｎｙｌｇｌｙｏｘａｌ ｂｉｓ（４-ｍｅｔｈｙｌ-３-ｔｈｉｏｓｅｍｉｃａｒｂａｚ' Ｊｏｕｒｎａｌ ｏｆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ ２１（８）, 1978, ８０４-８０９
JPN6015047633; Ｅ．Ｒ． Ｄｉｌａｎｙａｎ， Ｔ．Ｒ． Ｏｖｓｅｐｙａｎ， Ｆ．Ｇ． Ａｒｓｅｎｙａｎ， Ｇ．Ｍ． Ｓｔｅｐａｎｙａｎ， ａｎｄ Ｂ．Ｔ． Ｇａｒｉｂｄｚｈａｎｙａｎ: 'Ａｎｔｉｔｕｍｏｒ Ａｃｔｉｖｉｔｙ ｏｆ Ｓｕｂｓｔｉｔｕｔｅｄ Ｍｅｔｈｙｌｇｌｙｏｘａｌ Ｂｉｓｔｈｉｏｓｅｍｉｃａｒｂａｚｏｎｅ ａｎｄ ｔｈｅｉｒ Ｃｏｐｐｅｒ（ＩＩ） Ｃｈｅｌａｔｅｓ' Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｈｅｍｉｓｔｒｙ Ｊｏｕｒｎａｌ ４２（９）, 2008, ５０４-５０６
JPN6014001979; 'Ｍｉｘｅｄ Ｂｉｓ（ｔｈｉｏｓｅｍｉｃａｒｂａｚｏｎｅ） Ｌｉｇａｎｄｓ ｆｏｒ ｔｈｅ Ｐｒｅｐａ' Ｊ．Ｍｅｄ．Ｃｈｅｍ． ４０, 1997, １３２-１３６
JPN6015047626; Ｌｉｌｙ Ｊ． Ａｃｋｅｒｍａｎ， Ｄｏｕｇｌａｓ Ｘ． Ｗｅｓｔ， Ｃａｒｌａ Ｊ． Ｍａｔｈｉａｓ ａｎｄ Ｍａｒｋ Ａ． Ｇｒｅｅｎ: 'Ｓｙｎｔｈｅｓｉｓ ａｎｄ Ｅｖａｌｕａｔｉｏｎ ｏｆ Ｃｏｐｐｅｒ Ｒａｄｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ ｗｉｔｈ Ｍｉｘｅｄ Ｂｉｓ（ｔｈｏｓｅｍｉｃａｒｂａｚｏｎｅ） Ｌｉｇａｎｄｓ' Ｎｕｃｌｅａｒ Ｍｅｄｉｃｉｎｅ ＆ Ｂｉｏｌｏｇｙ ２６, 1999, ５５１-５５４
JPN6015047628; Ｊａｓｏｎ Ｐ． Ｈｏｌｌａｎｄ， Ｐｅｔｅｒ Ｊ． Ｂａｒｎａｒｄ， Ｓｉｍｏｎ Ｒ． Ｂａｙｌｙ，Ｈｅｌｅｎ Ｍ． Ｂｅｔｔｓ， Ｇｒａｎｔ Ｃ． Ｃｈｕｒｃｈｉｌｌ， Ｊｏｎａｔｈａｎ Ｒ． Ｄ: 'Ｓｙｎｔｈｅｓｉｓ， Ｒａｄｉｏｌａｂｅｌｌｉｎｇ ａｎｄ Ｃｏｎｆｏｃａｌ Ｆｌｕｏｒｅｓｃｅｎｃｅ Ｍｉｃｒｏｓｃｏｐｙ ｏｆ Ｓｔｙｒｅｎｅ-Ｄｅｒｉｖａｔｉｓｅｄ Ｂｉｓ（ｔｈｉｏｓｅｍｉｃａ' Ｅｕｒｏｐｅａｎ Ｊｏｕｒｎａｌ ｏｆ Ｉｎｏｒｇａｎｉｃ Ｃｈｅｍｉｓｔｒｙ １２, 2008, １９８５-１９９&
JPN6015047629; Ｄ．Ｗ． ＭｃＰｈｅｒｓｏｎ， Ｇ．Ｕｍｂｒｉｃｈｔ， ａｎｄ Ｆ． Ｆ． Ｋｎａｐｐ， Ｊｒ．: 'Ｒａｄｉｏｌａｂｅｌｌｉｎｇ ｏｆ Ｐｒｏｔｅｉｎｓ ｗｉｔｈ Ｒａｄｉｏｉｓｏｔｏｐｅｓ ｏｆ Ｃｏｐｐｅｒ ｕｓｉｎｇ ｐ-Ｃａｒｂｏｘｙａｌｋｙｌｐｈｅｎｙｌｇｌｙｏｘａｌ ｂｉｓ-（４Ｎ-Ｍｅ' Ｊｏｕｒｎａｌ ｏｆ Ｌａｂｅｌｌｅｄ Ｃｏｍｐｏｕｎｄｓ ａｎｄ Ｒａｄｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ ２８（８）, 1990, ８７７-８９９
JPN6015047631; Ｅｕｇｅｎｅ Ａ． Ｃｏａｔｓ， Ｓｔａｎｌｅｙ Ｒ． Ｍｉｌｓｔｅｉｎ， Ｍｉｃｈａｅｌ Ａ． Ｐｌｅｉｓｓ， ａｎｄ Ｊｅｆｆｒｅｙ Ａ． Ｒｏｅｓｅｎｅｒ: 'Ｃｏｍｐａｒａｔｉｖｅ Ａｎａｌｙｓｉｓ ｏｆ ｔｈｅ Ｃｙｔｏｔｏｘｉｃｉｔｙ ｏｆ Ｓｕｂｓｔｉｔｕｔｅｄ ［Ｐｈｅｎｙｌｇｌｙｏｘａｌ ｂｉｓ（４-ｍｅｔｈｙｌ-３-ｔｈｉｏｓｅｍｉｃａｒｂａｚ' Ｊｏｕｒｎａｌ ｏｆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ ２１（８）, 1978, ８０４-８０９
JPN6015047633; Ｅ．Ｒ． Ｄｉｌａｎｙａｎ， Ｔ．Ｒ． Ｏｖｓｅｐｙａｎ， Ｆ．Ｇ． Ａｒｓｅｎｙａｎ， Ｇ．Ｍ． Ｓｔｅｐａｎｙａｎ， ａｎｄ Ｂ．Ｔ． Ｇａｒｉｂｄｚｈａｎｙａｎ: 'Ａｎｔｉｔｕｍｏｒ Ａｃｔｉｖｉｔｙ ｏｆ Ｓｕｂｓｔｉｔｕｔｅｄ Ｍｅｔｈｙｌｇｌｙｏｘａｌ Ｂｉｓｔｈｉｏｓｅｍｉｃａｒｂａｚｏｎｅ ａｎｄ ｔｈｅｉｒ Ｃｏｐｐｅｒ（ＩＩ） Ｃｈｅｌａｔｅｓ' Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｈｅｍｉｓｔｒｙ Ｊｏｕｒｎａｌ ４２（９）, 2008, ５０４-５０６
Attorney, Agent or Firm:
Hajime Tsukuni