(+)-morphinanium quaternary salts and processes for their production

1. A compound of Formula (II):

wherein:

A is chosen from {—}C(O){—}, {—}C(═CH 2 ){—}, {—}CH 2 {—}, {—}CH(A 1 ){—}, and {—}C(A 1 ){=};

A 1 is chosen from hydroxy, alkoxy, acyloxy, amido, hydrocarbyl, and substituted hydrocarbyl;

R 1 , R 2 , and R 7 are independently chosen from hydrocarbyl and substituted hydrocarbyl;

R 3 and R 4 are independently chosen from hydrogen, hydrocarbyl and substituted hydrocarbyl;

R 5 and R 6 are independently chosen from hydrogen, hydrocarbyl, substituted hydrocarbyl, halogen, {—}OH, and {—}OR 7 ;

R 8 is chosen from hydrogen, hydrocarbyl, and substituted hydrocarbyl;

X is an anion;

Y, if present, is chosen from hydrogen, hydroxy, protected hydroxy, alkoxy, and acyloxy;

Z is chosen from hydroxy, protected hydroxy, alkoxy, and acyloxy; and

the dashed lines between the carbon atoms at positions 6 and 7, 7 and 8, and 8 and 14 represent carbon to carbon bonds chosen from (a) single bonds between all carbon atoms, wherein the carbons at positions 6 and 14 may be connected by an alkano bridge; (b) single bonds between the carbons at both positions 6 and 7 and 8 and 14, and a double bond between the carbons at positions 7 and 8; and (c) double bonds between the carbons at both positions 6 and 7 and 8 and 14, and a single bond between the carbons at positions 7 and 8, wherein Y is not present if there is a double bond between the carbons at positions 8 and 14.

2. The compound of claim 1 , wherein R 1 is chosen from alkyl, cycloalkyl, cycloalkylmethyl, allyl, and aryl; and R 2 is chosen from alkyl, allyl, alkenyl, and alkaryl and X is chosen from halide, sulfate, methylsulfate, ethylsulfate, benzenesulfonate, p-toluenesulfonate, fluoroborate, fiuorosulfonate, methylsulfonate, trifluoromethanesulfonate, hexachloroantimonate, hexafluorophosphate, and tetrafluoroborate.

3. The compound of claim 1 , wherein the compound has Formula (IIa):

wherein:

A is chosen from {—}C(O){—}, {—}C(═CH 2 ){—}, {—}CH 2 {—}, and {—}CH(A 1 ){—}, wherein the carbons at positions 6 and 14 may be connected by an alkano bridge;

A 1 is chosen from hydroxy, alkoxy, acyloxy, amido, hydrocarbyl, and substituted hydrocarbyl;

R 1 and R 2 are independently chosen from hydrocarbyl and substituted hydrocarbyl;

R 8 is chosen from hydrogen, hydroxy, alkyl, substituted alkyl, alkoxy, hydrocarbyl, and substituted hydrocarbyl;

X is an anion;

Y is chosen from hydrogen, hydroxy, alkoxy, and acyloxy; and

Z is chosen from hydroxy, alkoxy, and acyloxy.

4. The compound of claim 3 , wherein the compound is a quaternary salt of a compound chosen from (+)-dihydromorphine, (+)-dihydrocodeine, (+)-hydrocodone, (+)-hydromorphone, (+)-oxycodone, (+)-oxycodeinone, (+)-oxymorphone, (+)-oxymorphinone, (+)-naloxone, (+)-naltrexone, (+)-nalbuphine, (+)-nalfurafine, (+)-nalmefene, (+)-buprenorphine, and (+)-etorphine.

5. The compound of claim 1 , wherein the compound has Formula (IIb):

wherein:

A is chosen from {—}C(O){—}, {—}C(═CH 2 ){—}, {—}CH 2 {—}, and {—}CH(A 1 ){—};

A 1 is chosen from hydroxy, alkoxy, acyloxy, amido, hydrocarbyl, and substituted hydrocarbyl;

R 1 and R 2 are independently chosen from hydrocarbyl and substituted hydrocarbyl;

R 8 is chosen from hydrogen, hydroxy, alkyl, substituted alkyl, alkoxy, hydrocarbyl, and substituted hydrocarbyl;

X is an anion;

Y is chosen from hydrogen, hydroxy, alkoxy, and acyloxy; and

Z is chosen from hydroxy, alkoxy, and acyloxy.

6. The compound of claim 5 , wherein the compound is a quaternary salt of a compound chosen from (+)-morphine, (+)-codeine, and (+)-morphine-6-glucoronide.

7. The compound of claim 1 , wherein the compound has Formula (IIc):

wherein:

A 1 is chosen from hydrogen, hydroxy, alkoxy, acyloxy, amido, hydrocarbyl, and substituted hydrocarbyl;

R 1 and R 2 are independently chosen from hydrocarbyl and substituted hydrocarbyl;

R 8 is chosen from hydrogen, hydroxy, alkyl, substituted alkyl, alkoxy, hydrocarbyl, and substituted hydrocarbyl;

X is an anion; and

Z is chosen from hydroxy, alkoxy, and acyloxy.

8. The compound of claim 7 , wherein the compound is a quaternary salt of a compound chosen from (+)-thebaine and (+)-oripavine.