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US 9,426,989 B2Granted
Organic peroxide compounds for microorganism inactivation
AssigneeNovartis AG
InventorsJens Peter Gregersen, Thomas Grundemann
Life of this patent
Estimating the term…
Abstract
Multifunctional organic peroxides are used as microbiological inactivators and/or for degrading nucleic acids. These include at least one carbon atom and at least two organic peroxide groups. The inactivator is ideally a hydroperoxide. The invention is particularly useful during preparation of viral vaccines.
Claims35
A method for preparing a pharmaceutical composition, comprising steps of:
- (i) contacting a microorganism-containing sample with a multifunctional organic peroxide to inactivate microorganisms therein;
- and (ii) preparing a pharmaceutical composition from the product of step (i),
- wherein the multifunctional organic peroxide has a structure of one of the compounds of the following formula:
- where:
- R1a is H;
- R2a is H, C1-6alkyl, C2-6alkenyl, C1-6alkynyl, C1-6-alkoxy, C2-6-alkenyloxy, C(O)H, C(O)C1-6alkyl, C(O)OC1-6alkyl, amino, N-mono or N-di C1-6alkylated amino, aminocarbonyl, N-mono or N-di C1-6alkylated aminocarbonyl, S(O)0-2C1-6alkyl, heterocycloalkyl, aryl or heteroaryl, —(CR4R5)nCR6(OOH)2;
- R3 is H or C(OOH)R1bR2b,
- R1b is H, C1-6alkyl, C2-6alkenyl, C1-6alkynyl, C1-6-alkoxy, C2-6-alkenyloxy, C(O)H, C(O)C1-6alkyl, C(O)OC1-6alkyl, amino, N-mono or N-di C1-6alkylated amino, aminocarbonyl, N-mono or N-di C1-6alkylated aminocarbonyl, S(O)0-2C1-6alkyl, heterocycloalkyl, aryl or heteroaryl,
- R2b is H, C1-6 alkyl, C2-6alkenyl, C1-6alkynyl, C1-6-alkoxy, C2-6-alkenyloxy, C(O)H, C(O)C1-6alkyl, C(O)OC1-6alkyl amino, N-mono or N-di C1-6alkylated amino, aminocarbonyl, N-mono or N-di C1-6alkylated aminocarbonyl, S(O)0-2C1-6alkyl, heterocycloalkyl, aryl or heteroaryl, or
- R2b is linked to R2a by L, wherein L is C1-8alkylene;
- R4 is, at each occurrence, selected from H or C1-3 alkyl, hydroxyl, cyano, nitro, C2-4-alkenyl, C1-3-alkoxy, C2-4-alkenyloxy, C1-3-alkylcarbonyl, carboxy, C1-6-alkoxycarbonyl, aminocarbonyl, N-mono or N-di C1-3alkylated aminocarbonyl, C1-3-thioalkyl, C1-3-alkylsulfinyl, C1-3-alkylsulfonyl, C1-3-alkylaminosulfonyl and di-C1-3-alkylaminosulfonyl;
- R5 is, at each occurrence, selected from H or C1-3 alkyl, hydroxyl, cyano, nitro, C2-4-alkenyl, C1-3-alkoxy, C2-4-alkenyloxy, C1-3-alkylcarbonyl, carboxy, C1-6-alkoxycarbonyl, aminocarbonyl, N-mono or N-di C1-3alkylated aminocarbonyl, C1-3-thioalkyl, C1-3-alkylsulfinyl, C1-3-alkylsulfonyl, C1-3-alkylaminosulfonyl and di-C1-3-alkylaminosulfonyl;
- R6 is H C1-6alkyl, C2-6alkenyl, C1-6-alkoxy, C2-6-alkenyloxy, C(O)H, C(O)C1-6alkyl, C(O)OC1-6alkyl, amino, N-mono or N-di C1-6alkylated amino, aminocarbonyl, N-mono or N-di C1-6alkylated aminocarbonyl, S(O)0-2C1-6alkyl, heterocycloalkyl, aryl or heteroaryl;
- n is 1 to 8;
- and
- wherein the immunogenicity of the microorganisms is not reduced.
13 more elements
The method of claim where 1, where:
- R2a is H or C1-4alkyl or —(CH2)nCH(OOH)2 or is linked to R2b by L;
- and/or
- R1b is H or C1-4alkyl;
- and/or
- R2b is C1-4alkyl or is linked to R2a by L;
- R2b can thus be CH3, Et, or n-Pr;
- and/or
- each R4 is H or CH3;
- and/or
- each R5 is H or CH3;
- and/or
- L is C2-5alkylene;
- and/or
- R6 is H or C1-4alkyl;
- and/or
- n is 2 to 6.
13 more elements
Dependencies are inferred from the claim text.