Environmentally compatible detergents for inactivation of lipid-enveloped viruses

1. A compound which is the following compound:

wherein m equals 1 and z is an integer selected from the following group:

z=1 to 5.

2. The compound of claim 1 , wherein the compound is:

wherein n is an integer between 4 and 16.

3. A method for inactivating a virus having a lipid envelope, the method comprising the following steps:

a) adding a detergent to a liquid to prepare a mixture of said detergent and said liquid; and

b) incubating said mixture to inactivate said virus,

wherein said detergent is a polyoxyethylene ether, wherein said detergent is a non-phenolic detergent, and wherein the detergent is the compound of claim 1 .

4. The method of claim 3 , wherein said detergent is environmentally compatible.

5. The method of claim 3 , wherein step a) further comprises adding a solvent to said liquid, and wherein in step a), a solvent/detergent mixture for inactivation of said virus is prepared by adding said detergent and said solvent to said liquid.

6. The method of claim 5 , wherein said solvent is an organic solvent.

7. The method of claim 3 , wherein said liquid comprises a biological medicinal product and/or a biopharmaceutical drug.

8. The method of claim 7 , wherein said biopharmaceutical drug is a therapeutic protein.

9. The method of claim 3 , wherein:

(a) prior to step a) or between step a) and step b), said method further comprises a step of filtering said liquid or mixture with a depth filter;

(b) in step b), said mixture is incubated for at least 1 hour; and/or

(c) in step b), said mixture is incubated at a temperature of between 0° C. and 10° C., or

wherein said mixture is incubated at a temperature of between 16° C. and 25° C.

10. The method of claim 7 , further comprising, after step b), a step of

c) purifying said biopharmaceutical drug; and wherein:

(i) said purifying comprises separating said biopharmaceutical drug from said detergent;

and/or

(ii) said purifying of said biopharmaceutical drug comprises purifying said biopharmaceutical drug by at least one chromatographic purification.

11. A method for preparing a biopharmaceutical drug, said method comprising the method according to claim 7 , wherein said biopharmaceutical drug is as defined in claim 7 .

12. The method of claim 11 , further comprising a step of preparing a pharmaceutical formulation comprising said biopharmaceutical drug.

13. A composition comprising a detergent, wherein the detergent is the compound of claim 1 .

14. The composition of claim 13 further comprising an organic solvent.

15. A method for synthesizing a compound of the following general Formula (VIII),

wherein

R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain,

m equals 1, and

A represents a polyoxyethylene residue,

wherein the method comprises the steps of

A) Converting a phenol of the following general Formula (IX) wherein R is as defined above

 into an alcohol of the of the following general Formula (X) wherein R and m are as defined above

and

(B) converting the alcohol of the general Formula (X) into a polyoxyethylene ether of the general Formula (VIII) as defined above;

wherein the compound of Formula (VIII) is the following compound:

wherein m equals 1 and z is an integer selected from the following group:

z=1 to 5.

16. A method for synthesizing a compound of the following general Formula (VIII),

Wherein

R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain,

m equals 1, and

A represents a polyoxyethylene residue,

wherein the method comprises the steps of

(1) reacting toluene so as to obtain a substituted toluene of the following general Formula (XI) wherein R is as defined above

(2) converting the substituted toluene of the general Formula (XI) into a compound of the following general Formula (XII), wherein R and m are as defined above and X is selected from the group comprising a hydroxyl group, a bromine atom, an iodine atom and a chlorine atom

and

(3) converting the compound of the general Formula (XII) into a polyoxyethylene ether of the general Formula (VIII) as defined above;

wherein the compound of Formula (VIII) is the following compound:

wherein m equals 1 and z is an integer selected from the following group:

z=1 to 5.

17. A method for synthesizing a compound of the following general Formula (VIIIa),

wherein

R represents a hydrocarbon group having a linear chain of 2 to 12 carbon atoms and one or more methyl groups as substituents on said linear chain, and

A represents a polyoxyethylene residue,

wherein the method comprises the steps of

(I) converting benzyl alcohol into a compound of the following general Formula (XIII), wherein R is as defined above

and

(II) converting the compound of the general Formula (XIII) into a polyoxyethylene ether of the general Formula (VIIIa) as defined above;

wherein the compound of Formula (VIIIa) is the following compound:

wherein m equals 1 and z is an integer selected from the following group:

z=1 to 5.

18. The method of claim 15 , wherein the compound of Formula (VIII) is the following compound:

wherein n is an integer between 4 and 16.

19. The method of claim 16 , wherein:

(i) the converting in step (2) is a radical reaction using AIBN (Azobis(isobutyronitrile) as a radical initiator; and/or

(ii) X is a bromine atom.

20. The method of claim 16 , wherein:

(a) the converting in step (2) uses N-bromosuccinimide (NBS) as a reagent;

(b) the converting in step (3) uses TBME (methyl-tert-butylether) as a solvent;

(c) the converting in step (3) takes place for at least 2 hours;

(d) the converting in step (3) takes place for not more than 5 hours; and/or

(e) the converting in step (3) takes place for 3 hours.

21. The compound of claim 2 , wherein n is equal to 9 or 10.

22. The method of claim 6 , wherein said solvent is Tri-n-butyl phosphate.

23. The method of claim 8 , wherein said therapeutic protein is a blood factor, an immunoglobulin, a replacement enzyme, a vaccine, a gene therapy vector, a growth factor, or a growth factor receptor.

24. The method of claim 23 , wherein said immunoglobulin is a monoclonal antibody.

25. The method of claim 23 , wherein said blood factor is selected from the group consisting of factor I (fibrinogen), factor II (prothrom-bin), Tissue factor, factor V, factor VII or VIIa, factor VIII, factor IX, factor X, factor XI, factor XII, factor XIII, von Willebrand Factor (VWF), prekallikrein, high-molecular-weight kininogen (HMWK), fibronectin, antithrombin III, heparin cofactor II, protein C, protein S, protein Z, plasminogen, alpha 2-antiplasmin, tissue plasminogen activator (tPA), urokinase, plasminogen activator inhibitor-1 (PAI1), and plasminogen activator inhibitor-2 (PAI2).

26. The method of claim 25 , wherein the factor VIII is recombinant human factor VIII.

27. The method of claim 10 , wherein said at least one chromatographic purification is by anion exchange chromatography and/or by cation exchange chromatography.

28. The composition of claim 14 , wherein said solvent is Tri-n-butyl phosphate.

29. The method of claim 18 , wherein n is equal to 9 or 10.

30. The method of claim 20 , wherein the converting in step (3) takes place for at least 2 hours at ambient temperature.

31. The method of claim 20 , wherein the converting in step (3) takes place for not more than 5 hours at ambient temperature.

32. The method of claim 20 , wherein the converting in step (3) takes place for 3 hours at ambient temperature.