Syntheses of 10-Oxo, 10.ALPHA.-Hydroxy, and 10.BETA.-Hydroxy Derivatives of a Potent .KAPPA.-Opioid Receptor Agonist, TRK-820
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- Horikiri Hiromasa
- Pharmaceutical Research Laboratories, Toray Industries, Inc.
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- Hirano Noriyuki
- Pharmaceutical Research Laboratories, Toray Industries, Inc.
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- Tanaka Yoichiro
- Pharmaceutical Research Laboratories, Toray Industries, Inc.
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- Oishi Junji
- Pharmaceutical Research Laboratories, Toray Industries, Inc.
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- Hatakeyama Hitoshi
- Pharmaceutical Research Laboratories, Toray Industries, Inc.
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- Kawamura Kuniaki
- Pharmaceutical Research Laboratories, Toray Industries, Inc.
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- Nagase Hiroshi
- Pharmaceutical Research Laboratories, Toray Industries, Inc.
Bibliographic Information
- Other Title
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- Syntheses of 10-Oxo, 10α-Hydroxy, and 10β-Hydroxy Derivatives of a Potent κ-Opioid Receptor Agonist, TRK-820
- Syntheses of 10 Oxo 10 アルファ Hydroxy and 10 ベータ Hydroxy Derivatives of a Potent カッパ Opioid Receptor Agonist TRK 820
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Abstract
Syntheses of 10-oxo, 10α-hydroxy, and 10β-hydroxy derivatives of a potent κ-opioid receptor selective agonist, TRK-820, are described. These derivatives were supposed to be potential degradation products in formulation of TRK-820 as a result of autoxidation. 10-Oxo-TRK-820 11 was derived from 10-oxo-4,5-epoxymorphinan 14 in 10 steps in 32% overall yield. Reduction of the 10-oxo group in 4,5-epoxymorphinan with NaBH4 gave 10β-hydroxy-4,5-epoxymorphinan, exclusively. A stepwise inversion method of the 10β-hydroxy group to produce 10α-hydroxy-4,5-epoxymorphinan was established. By HPLC analyses, 10α-hydroxy-TRK-820 12 was confirmed to be one of the degradation products in developing formulation of TRK-820.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 52 (6), 664-669, 2004
The Pharmaceutical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282679146452224
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- NII Article ID
- 110003615638
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 6952842
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- PubMed
- 15187385
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed