IP Library Granted Patent US 8,367,735
Granted Patent B2
US 8,367,735 · App. 12/375,208 · Granted Feb 5, 2013

Pharmaceutical compositions

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Quick Facts
Patent No.
US 8,367,735
App. No.
12/375,208
Granted
Feb 5, 2013
Kind
B2
Abstract

The present invention relates to compounds of formula I or II:—wherein R is an alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, or aralkynyl group, that may be substituted or unsubstituted, and that optionally includes at least one heteroatom in its carbon skeleton; R 1 is hydrogen, or an alkyl, substituted alkyl, alkenyl, alkynyl, aryl, substituted aryl, or aralkyl group; and R 2 is an alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, or aralkynyl group containing 4-12 carbon atoms, that may be substituted or unsubstituted, and that optionally includes at least one heteroatom in its carbon skeleton; provided that in a compound of formula I, when R 1 is an iso-propyl or phenyl group, R 2 is not an acetyl or tert-butyldimethylsilyl group; and their use in therapeutic, diagnostic and research methods.

Claims (34)

1. A compound of II:

wherein:

R is an alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, or aralkynyl group, that may be substituted or unsubstituted, and that optionally includes at least one heteroatom in its carbon skeleton;

R 1 is hydrogen, or an alkyl, substituted alkyl, alkenyl, alkynyl, aryl, substituted aryl, or aralkyl group; and

R 2 is an alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, or aralkynyl group containing 4-12 carbon atoms, that may be substituted or unsubstituted, and that optionally includes at least one heteroatom in its carbon skeleton;

not an acetyl or tert-butyldimethylsilyl group.

2. A compound of formula II as claimed in claim 1 , wherein:

(a) R is an R 3 CH 2 — group, wherein R 3 is an alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, or aralkynyl group, that may be substituted or unsubstituted, and that optionally includes at least one heteroatom in its carbon skeleton;

(b) R contains 1-12 carbon atoms;

(c) R includes at least one hydrophilic group;

(d) R includes at least one hydrophilic group which is or includes a hydroxyl, carbonyl, carboxyl, amino, amido, quaternary ammonium or thiolyl group;

(e) R includes at least one hydrophilic group and provides the functionality of an amine, amide, peptide, ester, carboxylic acid, carboxylic acid salt, alcohol, aldehyde, ketone or thiol;

(f) the group —SR is an S-cysteinyl or a substituted S-cysteinyl group;

(g) the group —SR is a substituted S-cysteinyl group which is a di- or tri-peptide group that includes an S-cysteinyl moiety; or

(h) the group —SR is a substituted S-cysteinyl group which is an S-glutathionyl, N-tert-butoxycarbonyl S-cysteinyl or N-tert-butoxycarbonyl S-cysteinyl ester group.

3. A compound as claimed in claim 1 , wherein:

(a) R 1 is an aryl group; or

(b) R 1 is a phenyl group or a substituted phenyl group.

4. A compound as claimed in claim 1 , wherein:

(a) R 2 is an alkyl group that includes a heteroatom in its carbon skeleton;

(b) R 2 is an alkyl group that includes a silicon atom in its carbon skeleton;

(c) R 2 is a trialkylsilyl group;

(d) R 2 is a tert-butyldimethylsilyl group;

(e) R 2 is —COR 5 , wherein R 5 is an alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, or aralkynyl group containing 3-11 carbon atoms, that may be substituted or unsubstituted, and that optionally includes at least one heteroatom in its carbon skeleton;

(f) R 2 is —COR 5 , wherein R 5 is an alkyl group containing 3-6 carbon atoms; or

(g) R 2 is —COR 5 , wherein R 5 is a tert-butyl group.

5. A compound of formula II as claimed in claim 1 , having a calculated or measured Log P value that is at least 0.25, 0.5, 0.75, 1 or 1.25 higher or lower than the log P value for the equivalent compound of formula I, wherein the log P values for said compounds are calculated or measured using the same technique.

6. A compound as claimed in claim 1 :

(a) that is pharmaceutically or therapeutically active; or

(b) having activity in respect of one or more of the following: (i) activating HSF; (ii) inhibiting NF-κB; (iii) inhibiting the replication of HSV-1; (iv) inhibiting the replication of Sendai virus; (v) inducing apoptosis in cancer cell lines; and (vi) anti-angiogenic activity.

7. A pharmaceutical composition comprising a compound as claimed in claim 1 and optionally including a pharmaceutically acceptable carrier.

8. A food for an aquatic organism comprising a compound as claimed in claim 1 .

9. An aquatic environment comprising a compound as claimed in claim 1 .

10. The compound of claim 1 , wherein the compound is CTM-208 represented by the formula:

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2013
From: CRAWFORD HEALTHCARE HOLDINGS LIMITED
To: BIOGEM S.C.A.R.L.
Reel/Frame 030430/0867 →
CHANGE OF NAME Recorded Sep 4, 2012
From: RH ACQUISITIONS LIMITED
To: CRAWFORD HEALTHCARE HOLDINGS LIMITED
Reel/Frame 028897/0292 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 29, 2012
From: ROSANTO PHARMACEUTICALS LIMITED
To: RH ACQUISITIONS LIMITED
Reel/Frame 028870/0543 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 5, 2009
From: ROBERTS, STANLEY M.; SANTORO, GABRIELLA M.
To: ROSANTO PHARMACEUTICALS LTD.
Reel/Frame 022786/0840 →