SE7703236L - IMPROVED PROCEDURE FOR PREPARATION OF 14-HYDROXIMORFINAND DERIVATIVES - Google Patents

IMPROVED PROCEDURE FOR PREPARATION OF 14-HYDROXIMORFINAND DERIVATIVES

Info

Publication number
SE7703236L
SE7703236L SE7703236A SE7703236A SE7703236L SE 7703236 L SE7703236 L SE 7703236L SE 7703236 A SE7703236 A SE 7703236A SE 7703236 A SE7703236 A SE 7703236A SE 7703236 L SE7703236 L SE 7703236L
Authority
SE
Sweden
Prior art keywords
derivatives
hydroximorfinand
preparation
cyclobutylmethyl
methoxybenzyl
Prior art date
Application number
SE7703236A
Other languages
Swedish (sv)
Other versions
SE431749B (en
Inventor
I Monkovic
C Bachand
H Wong
G Lim
Original Assignee
Bristol Myers Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US05/669,795 external-priority patent/US4058531A/en
Priority claimed from US05/769,808 external-priority patent/US4139534A/en
Application filed by Bristol Myers Co filed Critical Bristol Myers Co
Publication of SE7703236L publication Critical patent/SE7703236L/en
Publication of SE431749B publication Critical patent/SE431749B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18—Aralkyl radicals
    • C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C07D221/28—Morphinans

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pain & Pain Management (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

N-substituted -14-hydroxy-3-substituted-morphinan derivatives have been found to possess potent narcotic agonist or antagonist activity. In particular, the compound N-Cyclo-butylmethyl-3,14-dihydroxymorpinan has been found to possess potent agonist/antagonist activity as a non-narcotic analgesic. An improved total synthesis of these compounds is described herein from the starting material 2-(p-methoxybenzyl)-1,2,3,4, 5,6,7,8-octahydroisoquinoline. A preferred feature of the process involves borane reduction of 2-cyclobutylcarbonyl-9,10-dihydroxy-1-(p-methoxybenzyl) perhydroisoquinoline (Va) to provide the corresponding cyclobutylmethyl derivative complexed with borane which is converted directly to N-cyclobutylmethyl-14.beta.-hydroxy-3-methoxymorphinan (LVa) by treating with acid.
SE7703236A 1976-03-23 1977-03-21 PROCEDURE FOR THE PREPARATION OF 14-HYDROXIMORPHINAND DERIVATIVE SE431749B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/669,795 US4058531A (en) 1976-03-23 1976-03-23 Process for the preparation of 14-hydroxymorphinan derivatives
US05/769,808 US4139534A (en) 1977-02-17 1977-02-17 Process for the preparation of 14-hydroxymorphinan derivatives

Publications (2)

Publication Number Publication Date
SE7703236L true SE7703236L (en) 1977-09-24
SE431749B SE431749B (en) 1984-02-27

Family

ID=27100195

Family Applications (1)

Application Number Title Priority Date Filing Date
SE7703236A SE431749B (en) 1976-03-23 1977-03-21 PROCEDURE FOR THE PREPARATION OF 14-HYDROXIMORPHINAND DERIVATIVE

Country Status (8)

Country Link
JP (1) JPS52136176A (en)
CA (1) CA1086723A (en)
CH (1) CH629783A5 (en)
DK (2) DK155322C (en)
FI (1) FI61486C (en)
LU (1) LU77000A1 (en)
NL (2) NL189846C (en)
SE (1) SE431749B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0373510U (en) * 1989-11-15 1991-07-24

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3634429A (en) * 1969-09-30 1972-01-11 Hoffmann La Roche Morphinan derivatives and preparation thereof
CA919668A (en) * 1970-06-20 1973-01-23 Murakami Masuo Morphinan derivatives
BE788478A (en) * 1971-09-08 1973-03-06 Bristol Myers Co PROCESS FOR PREPARING ANALGESIC COMPOUNDS
US3775414A (en) * 1972-05-10 1973-11-27 Bristol Myers Co Process for the preparation of 14-hydroxymorphinan derivatives

Also Published As

Publication number Publication date
CA1086723A (en) 1980-09-30
CH629783A5 (en) 1982-05-14
FI770865A (en) 1977-09-24
NL189846B (en) 1993-03-16
FI61486C (en) 1982-08-10
NL960022I1 (en) 1996-12-02
DK597188D0 (en) 1988-10-27
JPS6139938B2 (en) 1986-09-06
DK597188A (en) 1988-10-27
FI61486B (en) 1982-04-30
NL7703000A (en) 1977-09-27
DK155322B (en) 1989-03-28
LU77000A1 (en) 1977-10-03
DK155322C (en) 1989-09-11
JPS52136176A (en) 1977-11-14
SE431749B (en) 1984-02-27
NL189846C (en) 1993-08-16
DK160987C (en) 1991-11-11
DK160987B (en) 1991-05-13
DK123877A (en) 1977-09-24

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