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US 10,227,353 B2Granted
Compositions and methods for making alkaloid morphinans
AssigneeEpimeron Inc.
InventorPeter James Facchini
Life of this patent
Estimating the term…
Abstract
Methods that may be used for the manufacture of a class of chemical compounds known as morphinans, including neopine, are provided. Compositions useful for the synthesis of morphinans, including neopine, are also provided.
Claims6
A method of making a second morphinan having a C7-C8 saturated carbon bond and a C8-C14 mono-unsaturated carbon bond comprising:
- (a) providing a first morphinan having a C7-C8 mono-unsaturated carbon bond and a C8-C14 saturated carbon bond;
- and
- (b) contacting the first morphinan with a codeine isomerase or codeinone reductase capable of converting the first morphinan into the second morphinan;
- wherein
- the first morphinan has the chemical formula (V)
- and wherein the second morphinan has the chemical formula (VI)
- and wherein in the first and second morphinan R1 is a methoxy group, R2 is a hydroxyl group and R2′ a hydrogen atom;
- or
- the first morphinan has the chemical formula (V)
- and wherein the second morphinan has the chemical formula (VI)
- and wherein in the first and second morphinan R1 is a hydroxyl group, R2 is a hydroxyl group and R2′ is a hydrogen atom;
- or
- the first morphinan has the chemical formula (VII)
- and wherein the second morphinan has the chemical formula (VIII)
- and wherein in the first and second morphinan R1 is a methoxy group, R2 is a hydroxyl group and R2′ is a hydrogen atom;
- or
- the first morphinan has the chemical formula (VII)
- and wherein the second morphinan has the chemical formula (VIII)
- and wherein in the first and second morphinan R1 is a hydroxyl group, R2 is a hydroxyl group and R2′ is a hydrogen atom;
- or
- the first morphinan has the chemical formula (IX)
- and wherein the second morphinan has the chemical formula (X)
- and wherein in the first and second morphinan R1 is a methoxy group, R2 is a hydroxyl group and R2′ is a hydrogen atom;
- or
- the first morphinan has the chemical formula (IX)
- and wherein the second morphinan has the chemical formula (X)
- and wherein in the first and second morphinan R1 is a hydroxyl group, R2 is a hydroxyl group and R2′ is a hydrogen atom.
24 more elements
A method for preparing a morphinan having chemical formula (II)
- wherein, R1 represents a hydroxyl group or a methoxy group;
- wherein R2 represents a hydroxyl group and R2′ represents a hydrogen atom;
- and wherein R3 represents a hydrogen atom, or a methyl group, wherein when R3 represents a methyl group, the nitrogen atom bonded to R3 is optionally in the form of an N-oxide;
- and wherein the method comprises:
- (a) providing a chimeric nucleic acid sequence comprising as operably linked components:
- (i) a nucleic acid sequence encoding a codeine isomerase polypeptide or codeinone reductase polypeptide;
- (ii) one or more nucleic acid sequences capable of controlling expression in a host cell;
- (b) introducing the chimeric nucleic acid sequence into a host cell that endogenously produces or is exogenously supplied with a morphinan substrate;
- (c) growing the host cell to produce codeine isomerase or codeinone reductase and to produce the morphinan having chemical formula (II);
- and
- (d) recovering the morphinan having chemical formula (II) from the cell.
8 more elements
Dependencies are inferred from the claim text.