O-DEMETHYLATION OF OPIOID DERIVATIVES WITH METHANE SULFONIC-ACID METHIONINE - APPLICATION TO THE SYNTHESIS OF NALOXONE AND ANALOGS

被引：17

作者：

ANDRE, JD

DORMOY, JR

HEYMES, A

机构：

[1] Sanofi-Chimie, Sisteron, cedex, Route de Gap

来源：

SYNTHETIC COMMUNICATIONS | 1992年 / 22卷 / 16期

关键词：

D O I：

10.1080/00397919208019086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Naloxone 2 was obtained by demethylation of N-allylnoroxycodone 1 with methane sulfonic acid/methionine. This reagent is an excellent substitute for boron tribromide. It was used for the synthesis of analogous derivatives with variable results.

引用

页码：2313 / 2327

页数：15

共 30 条

[11] NARCOTIC-ANTAGONISTS .4. CARBON-6 DERIVATIVES OF N-SUBSTITUTED NOROXYMORPHONES AS NARCOTIC-ANTAGONISTS
HAHN, EF
FISHMAN, J
HEILMAN, RD
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (03) : 259 - 262
[12] ANALGESICS OF THE ORVINOL TYPE - 19-DEOXY AND 6,20-EPOXY DERIVATIVES
HUTCHINS, CW
RAPOPORT, H
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (04) : 521 - 527
[13] IIJIMA I, 1978, J MED CHEM, V21, P398
[14] ROLE OF METHIONINE IN FACILITATED CLEAVAGE OF AROMATIC ETHERS BY METHANESULPHONIC ACID
IRIE, H
FUJII, N
OGAWA, H
YAJIMA, H
FUJINO, M
SHINAGAWA, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (22) : 922 - 923
[15] IRIE H, 1977, CHEM PHARM BULL, V25, P2929
[16] KISO Y, 1979, PEPTIDE CHEM, P25
[17] KISO Y, 1980, PROTEIN RES F, P193
[18] ANALGESICS OF THE 6,14-ETHENOMORPHINAN TYPE - 6-DEOXY-7ALPHA-ORVINOLS AND 6-DEOXY-8ALPHA-ORVINOLS
KNIPMEYER, LL
RAPOPORT, H
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (04) : 461 - 466
[19] SYNTHESIS OF MORPHINE-D5 AND CODEINE-D8
LAWSON, JA
DEGRAW, JI
ANBAR, M
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (03) : 593 - 595
[20] Olofson R.A, 1979, U.S. Patent, Patent No. [4,141,897, 4141897]

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