Derivatives of polyhydroxy compounds

Patent metadata

Field	Value
Publication number	US-9796659-B2
Application number	US-201515112683-A
Country	US
Kind code	B2
Filing date	Feb 27, 2015
Priority date	Feb 27, 2014
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

The present invention relates to novel compounds, e.g. for use as a medicament. In particular, the present invention relates to novel prodrugs of monomethyl fumarate (MMF) suitable as a medicament, preferably in the treatment and/or prevention of systemic diseases, autoimmune diseases, inflammatory diseases, for example multiple sclerosis and psoriasis.

First claim

The invention claimed is:

1. A compound according to one of Formula (II) or Formula (IIa):

wherein R 4 is trans —CO—CH═CH—COOCH 3 ;
R 5 is —(CH 2 ) n —COR 51 or —(CH 2 ) n —OH with n being 0, 1 or 2, wherein
R 51 is —OR 52 or NR 53 R 54 wherein R 52 , R 53 and R 54 are independently hydrogen or alkyl with 1 to 4 carbon atoms;
R 5 ′ and R 5 ″ taken together are ═O, ═S or NR 100 , wherein R 100 is hydrogen or alkyl with 1 to 4 carbon atoms.

2. Compound according to claim 1 , wherein in Formula (II) R 5 is —(CH 2 ) n —OH with n being 0, 1 or 2.

3. Compound according to claim 1 , wherein the compound according to Formula (II) is the compound according to of Formula (VII)

4. Pharmaceutical composition comprising a compound according to claim 1 .

5. Pharmaceutical composition according to claim 4 comprising
(i) 0.01 to 10 mmol of the compound; and
(ii) optionally pharmaceutical excipients.

6. Pharmaceutical composition according to claim 4 , wherein the composition is a solid oral dosage form.

7. Pharmaceutical composition according to claim 4 , wherein an in-vitro drug release after 2 hours is less than 10%, measured according to USP, Apparatus II, paddle, 0.1 HCl, 37° C., 50 rpm.

8. Is subject in need thereof a therapeutically effective amount of a compound according to claim 1 .

Assignees

• Ratiopharm Gmbh

Inventors

• Albrecht Wolfgang
• Lehmann Frank
• Selig Roland
• Rabe Sebastian
• Maier Annemarie
• Guserle Richard

Classifications

• A61P17/06

  Antipsoriatics · CPC title

• C07C69/604

  Polycarboxylic acid esters, the acid moiety containing more than two carboxyl groups · CPC title

• C07C69/60 Primary

  Maleic acid esters; Fumaric acid esters · CPC title

• A61K31/225

  Polycarboxylic acids · CPC title

• A61K9/0053

  Mouth and digestive tract, i.e. intraoral and peroral administration · CPC title