US 2009/0156818 A1Published application

Process and compounds for the production of (+)opiates

AssigneeMallinckrodt Inc.

InventorsPeter X. Wang, Tao Jiang, Gary L. Cantrell, David W. Berberich, Bobby N. Trawick, Todd Osiek, Subo Liao, Frank W. Moser, Joseph P. Mcclurg

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Abstract

The invention generally provides processes and intermediate compounds useful for the production of (+)-opiates. Non-limiting examples of (+) opiates that may be derived from one or more compounds of the invention include (+)-noroxymorphone, (+)-naltrexone, (+)-naloxone, (+)-N-cyclopropylmethylnorhydrocodone, (+)-N-cycloproylmethylnorhydromorphone, (+)-N-allylnorhydrocodone, (+)-N-allylnorhydromorphone, (+)-noroxycodone, (+)-naltrexol, (+)-naloxol, and (+)-3-O-methyl-naltrexone.

Claims25

Dependent claims

A compound comprising formula (I):

wherein:
R1 is selected from the group consisting of hydrogen, and {—}OCOR5;
R2 is selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl;
R3 is selected from the group consisting of hydrogen, {—}OCOR6, {—}OCR6, and a bond that forms part of an ether-containing ring, provided, however, if R3 is a bond forming an ether-containing ring then compound (I) is the (+) enantiomer;
R4 is selected from the group consisting of {—}OR7 and hydrogen;
R5 and R6 are independently selected from the group consisting of hydrocarbyl and substituted hydrocarbyl;
R7 is selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl;
R8 and R9 are independently selected from the group consisting of hydrogen, hydroxy, hydrocarbyl, and substituted hydrocarbyl, or R8 and R9 together form a carbonyl group;
R10 and R11 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, and a halogen;
and
is a single bond or a double bond.

8 more elements

A process for the preparation of compound (Ib) according to the following reaction scheme:

wherein:
R is selected from hydrocarbyl, and substituted hydrocarbyl;
R1 is selected from the group consisting of hydrogen and {—}OCOR5;
R3 is selected from the group consisting of hydrogen, {—}OCOR6, and {—}OCR6;
R5 and R6 are independently selected from the group consisting of hydrocarbyl and substituted hydrocarbyl;
R8 and R9 are independently selected from the group consisting of hydrogen, hydroxyl, hydrocarbyl, and substituted hydrocarbyl, or R8 and R9 together form a carbonyl group;
R12, and R13 are independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl, or R12 and R13 together form a carbonyl group;
R10, R11, and R14 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, and a halogen;
R15 is hydrogen;
and
X is a halogen.

8 more elements

A process for the preparation of compound (Ib) according to the following reaction scheme:

wherein:
R is selected from hydrocarbyl, and substituted hydrocarbyl;
R1 is selected from the group consisting of hydrogen and {—}OCOR5;
R3 is selected from the group consisting of hydrogen, {—}OCOR6, and {—}OCR6;
R5 and R6 are independently selected from the group consisting of hydrocarbyl and substituted hydrocarbyl;
R8 and R9 are independently selected from the group consisting of hydrogen, hydroxyl, hydrocarbyl, and substituted hydrocarbyl, or R8 and R9 together form a carbonyl group;
R12, and R13 are independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl, or R12 and R13 together form a carbonyl group;
R10, R11, and R14 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, and a halogen;
R15 is hydrogen;
and
X is a halogen.

8 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/316,862Filed 17 Dec 2008
Priority: 17 Dec 2007
Published: 18 Jun 2009
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 221/22
Condensed with carbocyclic rings or ring systems: bridged ring systems
A61P 25/04
Drugs for disorders of the nervous system: centrally acting analgesics, e.g. opioids
C07D 489/04
With oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone: salts; Organic complexes
C07D
Heterocyclic compounds