3m Innovative Properties Company

Paul D Wightman

Ross M Kedl

Isidro Angelo E Zarraga

Jie Jerry Liu

Naiyong Jing

George W Griesgraber

Mark A Tomai

Richard L Miller

Minghua Dai

James D Stoesz

Ronnie Ortiz

Dmitri V Smirnov

Isidro Angelo Eleazar Zarraga

The compound N-(4-{[4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butyl)octadecanamide is a useful drug compound for enhancing immune response and can be used, for example, as a coronavirus vaccine adjuvant.

Lipidated immune response modifier compound compositions, formulations, and methods

The compound N-(4-{[4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butyl)octadecanamide is a useful drug compound for enhancing immune response and can be used, for example, as a vaccine adjuvant and a cancer treatment.

Conjugates of an immune response modifier, a linker, and an antigen are disclosed. The linker is represented by formula:  wherein A is CH or N, p is in a range from 1 to 50, R&#x2033; is a bond or -alkylene-O&#x2014;, R' is alkylene that is optionally interrupted or terminated with one or more amide or ether groups, and E is an amine- or thiol-reactive group. Pharmaceutical compositions containing the compound or the conjugate, methods of making a conjugate, and methods of use of the compounds or conjugates as immunomodulators for inducing cytokine biosynthesis in an animal and for vaccinating an animal are also disclosed. An antigen modified by the linker is also disclosed.

Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom

1H-Imidazo[4,5-c]quinolin-4-amines substituted at the 1-position with a substituent bearing a hydrazinobenzamide or hydrazinonicotinamide, a salt thereof, or a protected hydrazinobenzamide or hydrazinonicotinamide and conjugates made from such compounds are disclosed. Pharmaceutical compositions containing the compound or the conjugate, methods of making a conjugate, and methods of use of the compounds or conjugates as immunomodulators for inducing cytokine biosynthesis in an animal and for vaccinating an animal are also disclosed.

Hydrazino 1H-imidazoquinolin-4-amines and conjugates made therefrom

Conjugates of an immune response modifier, a linker, and an antigen are disclosed. The linker is represented by formula: wherein A is CH or N, p is in a range from 1 to 50, R&#x2033; is a bond or -alkylene-O&#x2014;, R' is alkylene that is optionally interrupted or terminated with one or more amide or ether groups, and E is an amine- or thiol-reactive group. Pharmaceutical compositions containing the compound or the conjugate, methods of making a conjugate, and methods of use of the compounds or conjugates as immunomodulators for inducing cytokine biosynthesis in an animal and for vaccinating an animal are also disclosed. An antigen modified by the linker is also disclosed.

Methods and compositions for enhancing the immune response to an IRM compound by depositing within a localized tissue region an IRM depot preparation that provides an extended residence time of active IRM within the localized tissue region.

Methods and compositions for enhancing immune response

The compound N-(4-{[4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxyl}butyl)octadecanamide is a useful drug compound for enhancing immune response and can be used, for example, as a vaccine adjuvant and a cancer treatment.

Skin penetration enhancers comprising peptides are disclosed. Compositions comprising the skin penetration enhancers are also provided. The compositions further comprise an active agent, such as a pharmaceutically active agent, a vaccine, a cosmetic agent, and a. nutritional supplement. Methods of transdermal ly delivering a pharmaceutically active agent, a vaccine, a cosmetic agent, or a nutritional supplement are also provided.

Peptides for enhancing transdermal delivery

Conjugates of an immune response modifier, a linker, and an antigen are disclosed. The linker is represented by formula (I): wherein A is CH or N, p is in a range from 1 to 50, R&#x2033; is a bond or -alkylene-O&#x2014;, R' is alkylene that is optionally interrupted or terminated with one or more amide or ether groups, and E is an amine- or thiol-reactive group. Pharmaceutical compositions containing the compound or the conjugate, methods of making a conjugate, and methods of use of the compounds or conjugates as immunomodulators for inducing cytokine biosynthesis in an animal and for vaccinating an animal are also disclosed. An antigen modified by the linker is also disclosed. 

The present invention provides immune response modifiers (IRMs) associated with (typically, attached to, and preferably, covalently attached to) macromolecular support materials. The IRM compounds in such IRM-support complexes retain biological activity. Such attachment of an IRM to a macromolecular support material provides for the localized biological activity of the IRM.

Growing community of inventors

Louisville, KY, United States of America

Paul D Wightman