Abstract: Improved methods of treating multiple sclerosis and/or psoriasis using prodrugs of methyl hydrogen fumarate are disclosed. The methods comprise administering certain prodrugs of methyl hydrogen fumarate. The methods are able to achieve high blood plasma concentrations of the active metabolite, methyl hydrogen fumarate, without causing significant gastrointestinal irritation. New prodrugs of methyl hydrogen fumarate are also disclosed.
Type:
Application
Filed:
May 31, 2018
Publication date:
September 27, 2018
Applicant:
XenoPort, Inc.
Inventors:
Peter A. Virsik, David J. Wustrow, Thamil Annamalai, Suresh K. Manthati
Abstract: Improved methods of treating multiple sclerosis and/or psoriasis using prodrugs of methyl hydrogen fumarate are disclosed. The methods comprise administering certain prodrugs of methyl hydrogen fumarate. The methods are able to achieve high blood plasma concentrations of the active metabolite, methyl hydrogen fumarate, without causing significant gastrointestinal irritation. New prodrugs of methyl hydrogen fumarate are also disclosed.
Type:
Application
Filed:
April 19, 2018
Publication date:
August 23, 2018
Applicant:
XenoPort, Inc.
Inventors:
Peter A. Virsik, David J. Wustrow, Thamil Annamalai, Suresh K. Manthati
Abstract: Pharmaceutical compositions and dosage forms of (N,N-diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate and/or methyl 4-morpholin-4-ylbutyl (2E)but-2-ene-1,4-dioate, containing low levels of certain impurities are disclosed.
Type:
Grant
Filed:
March 20, 2015
Date of Patent:
June 19, 2018
Assignee:
XENOPORT, INC.
Inventors:
Suresh Kumar Manthati, Sami Karaborni, Wei Chen
Abstract: Sustained release oral dosage forms of a gabapentin prodrug, 1-{[(?-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid, are disclosed. The dosage forms are useful for treating or preventing diseases and disorders for which gabapentin is therapeutically effective.
Type:
Grant
Filed:
November 22, 2016
Date of Patent:
April 24, 2018
Assignee:
XENOPORT, INC.
Inventors:
Kenneth C. Cundy, Srikonda Sastry, Manshiu Leung, Balaji V. Kadri, Paul E. Stach
Abstract: The disclosures herein relate generally to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, pharmaceutical compositions thereof, methods of making prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, methods of using prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing common diseases and/or disorders such as spasticity and/or acid reflux disease. The disclosures herein also relate to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof which are suitable for oral administration and to sustained release oral dosage forms thereof.
Type:
Grant
Filed:
December 22, 2016
Date of Patent:
April 17, 2018
Assignee:
XENOPORT, INC.
Inventors:
Mark A. Gallop, Fenmei Yao, Maria J. Ludwikow, Thu Phan, Ge Peng
Abstract: Disclosed herein are crystalline forms of (N,N-Diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate, which is a prodrug of methyl hydrogen fumarate. Crystalline form 1, Crystalline form 2, Crystalline 3, and Crystalline form 4 are disclosed.
Type:
Grant
Filed:
September 6, 2017
Date of Patent:
February 20, 2018
Assignee:
XENOPORT, INC.
Inventors:
Chen Mao, Randall A. Scheuerman, Sami Karaborni
Abstract: Disclosed herein are crystalline forms of (N,N-Diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate, which is a prodrug of methyl hydrogen fumarate. Crystalline form 1, Crystalline form 2, Crystalline 3, and Crystalline form 4 are disclosed.
Type:
Grant
Filed:
May 8, 2017
Date of Patent:
October 24, 2017
Assignee:
XENOPORT, INC.
Inventors:
Chen Mao, Randall A. Scheuerman, Sami Karaborni
Abstract: The disclosures herein relate generally to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, pharmaceutical compositions thereof, methods of making prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, methods of using prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing common diseases and/or disorders such as spasticity and/or acid reflux disease. The disclosures herein also relate to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof which are suitable for oral administration and to sustained release oral dosage forms thereof.
Type:
Application
Filed:
December 22, 2016
Publication date:
July 6, 2017
Applicant:
XENOPORT, INC.
Inventors:
Mark A. Gallop, Fenmei Yao, Maria J. Ludwikow, Thu Phan, Ge Peng
Abstract: Disclosed herein are crystalline forms of (N,N-Diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate, which is a prodrug of methyl hydrogen fumarate. Crystalline form 1, Crystalline form 2, Crystalline 3, and Crystalline form 4 are disclosed.
Type:
Grant
Filed:
July 20, 2016
Date of Patent:
June 20, 2017
Assignee:
XENOPORT, INC.
Inventors:
Chen Mao, Randall A. Scheuerman, Sami Karaborni
Abstract: Improved oral dosage forms of methyl hydrogen fumarate and prodrugs thereof are disclosed. Methods of treating diseases such as multiple sclerosis and psoriasis using such dosage forms are also disclose.
Type:
Application
Filed:
January 7, 2016
Publication date:
June 8, 2017
Applicant:
XENOPORT, INC.
Inventors:
Sami Karaborni, Sarina Grace Harris Ma, Chen Mao, Ching Wah Chong, Peter Robert Prinz Freed, Mesut Ciper, Stefanie Krenzlin, David J. Wustrow, Peter A. Virsik
Abstract: Improved oral dosage forms of methyl hydrogen fumarate and prodrugs thereof are disclosed. Methods of treating diseases such as multiple sclerosis and psoriasis using such dosage forms are also disclosed.
Type:
Grant
Filed:
August 22, 2013
Date of Patent:
March 21, 2017
Assignee:
XenoPort, Inc.
Inventors:
Sami Karaborni, Sarina Grace Harris Ma, Chen Mao, Ching Wah Chong, Peter Robert Prinz Freed, Mesut Ciper, Stefanie Krenzlin, David J. Wustrow, Peter A. Virsik
Abstract: Disclosed herein are crystalline forms of (N,N-Diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate, which is a prodrug of methyl hydrogen fumarate. Crystalline form 1, Crystalline form 2, Crystalline 3, and Crystalline form 4 are disclosed.
Type:
Application
Filed:
July 20, 2016
Publication date:
February 16, 2017
Applicant:
XenoPort, Inc.
Inventors:
Chen Mao, Randall A. Scheuerman, Sami Karaborni
Abstract: Prodrugs of methyl hydrogen fumarate, pharmaceutical compositions comprising prodrugs of methyl hydrogen fumarate, and methods of using prodrugs of methyl hydrogen fumarate and pharmaceutical compositions thereof for treating diseases such as psoriasis, asthma, multiple sclerosis, inflammatory bowel disease, and arthritis are disclosed.
Type:
Grant
Filed:
June 6, 2014
Date of Patent:
September 27, 2016
Assignee:
XenoPort, Inc.
Inventors:
Archana Gangakhedkar, Xuedong Dai, Noa Zerangue, Peter A. Virsik
Abstract: Disclosed herein are crystalline forms of (N,N-Diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate, which is a prodrug of methyl hydrogen fumarate. Crystalline form 1, Crystalline form 2, Crystalline 3, and Crystalline form 4 are disclosed.
Type:
Grant
Filed:
September 5, 2014
Date of Patent:
August 16, 2016
Assignee:
XenoPort, Inc.
Inventors:
Chen Mao, Randall A. Scheuerman, Sami Karaborni
Abstract: Methods for synthesis of 1-(acyloxy)-alkyl carbamates, particularly, the synthesis of 1-(acyloxy)-alkyl carbamate prodrugs of primary or secondary amine-containing drugs are described. Also described are methods for synthesis of 1-(acyloxy)-alkyl N-hydroxysuccinimidyl carbonates which are useful intermediates in the synthesis of 1-(acyloxy)-alkyl carbamates are also described.
Type:
Grant
Filed:
January 15, 2013
Date of Patent:
May 31, 2016
Assignee:
XenoPort, Inc.
Inventors:
Mark A. Gallop, Xuedong Dai, Randall A. Scheuerman, Stephen P. Raillard, Suresh K. Manthati, Fenmei Yao, Thu Phan, Maria Ludwikow, Ge Peng, Seema Bhat
Abstract: Improved oral dosage forms of methyl hydrogen fumarate and prodrugs thereof are disclosed. Methods of treating diseases such as multiple sclerosis and psoriasis using such dosage forms are also disclose.
Type:
Application
Filed:
January 7, 2016
Publication date:
April 28, 2016
Applicant:
XENOPORT, INC.
Inventors:
Sami Karaborni, Sarina Grace Harris Ma, Chen Mao, Ching Wah Chong, Peter Robert Prinz Freed, Mesut Ciper, Stefanie Krenzlin, David J. Wustrow, Peter A. Virsik
Abstract: Methods of making monomethyl fumarate, which can then also be used in methods of making prodrugs of monomethyl fumarate, are disclosed. Monomethyl fumarate and prodrugs of monomethyl fumarate are useful for treating neurodegenerative, inflammatory, and autoimmune diseases including multiple sclerosis, psoriasis, irritable bowel disorder, ulcerative colitis, arthritis, chronic obstructive pulmonary disease, asthma, Parkinson's disease, Huntington's disease, and amyotrophic lateral sclerosis.
Type:
Grant
Filed:
June 6, 2014
Date of Patent:
April 5, 2016
Assignee:
XenoPort, Inc.
Inventors:
Stephen P. Raillard, Randall A. Scheuerman, Suresh K. Manthati