Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 62, Issue 4, Pages 354-363Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c13-00961
Keywords
diisobutylaluminum hydride; ring-expansion rearrangement; cyclic oxime; urate transporter-1 (URAT-1) inhibitor; arginine vasopressin (AVP) antagonist; 17 beta-hydroxysteroid dehydrogenase type-3 (17 beta-HSD3) inhibitor
Funding
- KAKENHI [23590001]
- Cabinet Office, Government of Japan
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- JSPS
- Japan Tobacco Inc.
- Banyu Life Science Foundation International
- Grants-in-Aid for Scientific Research [26253001, 23590001] Funding Source: KAKEN
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Synthesis of three clinical candidates for medicines, a human urate transporter-1 inhibitor, an arginine vasopressin antagonist, and a 17 beta-hydroxysteroid dehydrogenase type-3 inhibitor, is described. These compounds were synthesized via construction of their 3,4-dihydro-2H-benzo[b][1,4]oxazine, dibenzodiazepine, and dibenzazocine skeletons, respectively, using the reductive ring-expansion reaction of the corresponding bicyclic or tricyclic oximes with diisobutylaluminum hydride.
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