6'-deoxy-6'-halo-neplanocin A and its production

• US 5,187,174 A
• Filed: 03/18/1991
• Issued: 02/16/1993
• Est. Priority Date: 02/14/1989
• Status: Expired due to Fees

• Current Assignee: Asahi Kasei Kogyo Kabushiki Kaisha (Asahi Kasei Corporation)
• Original Assignee: Asahi Kasei Kogyo Kabushiki Kaisha (Asahi Kasei Corporation)
• Inventors: Obara, Takumi, Shuto, Satoshi, Koshio, Takehiro, Fujiwara, Tatsuro, Itoh, Hiromichi, Yaso, Masao
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): GRUMBLING, MATTHEW V
• Application Number:
  US07/673,177
• Time in Patent Office: 701 Days
• Field of Search: 544/277, 514/261
• US Class Current: 514/263.4
• CPC Class Codes: C07D 473/00 Heterocyclic compounds containing purine ring systems
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

A compound of the formula ##STR1## wherein A is adenine-9-yl and X is halogen, Preferably iodine, or a pharmaceutically acceptable salt thereof. It is a novel derivative of neplanocin A and has almost the same level of cytotoxic activity. However, it is not inactivated by the action of adenosine deaminase. It is produced by replacing a hydroxyl at position-6'"'"' in neplanocin A or 2'"'"', 3'"'"'-O-protected neplanocin A with halogen by use of a halogenating agent, and when hydroxyl at position-2'"'"' or -3'"'"' is protected, removing the protective group thereof.

Claims

1. A compound of the formula ##STR6## wherein A is adenine-9-yl and X is halogen, or a pharmaceutically acceptable salt thereof, said compound or salt being isolated from other compounds present during its production.

2. A pharmaceutical composition for producing a cytotoxic effect, comprising:

a compound of the formula ##STR7## wherein A is adenine-9-yl and X is halogen, or a pharmaceutically acceptable salt of said compound;

in combination with a pharmaceutical diluent;

said compound or salt being present in an amount effective to produce a cytotoxic effect.