Methimazole derivatives and tautomeric cyclic thiones to treat autoimmune diseases
First Claim
Patent Images
1. A pharmaceutical composition comprising a safe and effective amount of a compound selected from wherein Y is selected from the group consisting of H, C1-C4 alkyl, C1-C4 substituted alkyl, —
- NO2, and the phenyl moiety
and wherein no more than one Y group in said active compound may be the phenyl moiety;
R1 is selected from the group consisting of H, —
OH, C1-C4 alkyl, and C1-C4 substituted alkyl;
R2 is selected from the group consisting of H, C1-C4 alkyl and C1-C4 substituted alkyl;
R3 is selected from the group consisting of H, C1-C4 alkyl, C1-C4 substituted alkyl, and —
CH2Ph;
R4 is selected from the group consisting of H, C1-C4 alkyl, and C1-C4 substituted alkyl;
X is selected from S and O; and
Z is selected from —
SR3 , —
OR3 and C1-C4 alkyl; and
wherein at least two of the R2 and R3 groups in said compound are C1-C4 alkyl when Y is not a phenyl moiety, and at least one Y is —
NO2 when Z is alkyl; and
a pharmaceutically-acceptable carrier.
9 Assignments
0 Petitions
Accused Products
Abstract
The present invention provides methods for treating autoimmune diseases in mammals and for preventing or treating transplantation rejection in a transplant recipient. These methods utilize specifically-defined methimazole derivatives and tautomeric cyclic thione compounds, as well as pharmaceutical compositions containing those compounds. These compounds and compositions have been found to be at least as effective as methimazole in terms of pharmaceutical activity, while having less of an adverse affect on thyroid function. They are also more soluble in conventional pharmaceutical vehicles than methimazole. An assay for screening the activity of compounds useful against autoimmune diseases (ability to suppress expression of MHC Class I and II molecules) is also taught.
59 Citations
44 Claims
-
1. A pharmaceutical composition comprising a safe and effective amount of a compound selected from
wherein Y is selected from the group consisting of H, C1-C4 alkyl, C1-C4 substituted alkyl, — - NO2, and the phenyl moiety
and wherein no more than one Y group in said active compound may be the phenyl moiety;
R1 is selected from the group consisting of H, —
OH, C1-C4 alkyl, and C1-C4 substituted alkyl;
R2 is selected from the group consisting of H, C1-C4 alkyl and C1-C4 substituted alkyl;
R3 is selected from the group consisting of H, C1-C4 alkyl, C1-C4 substituted alkyl, and —
CH2Ph;
R4 is selected from the group consisting of H, C1-C4 alkyl, and C1-C4 substituted alkyl;
X is selected from S and O; and
Z is selected from —
SR3 , —
OR3 and C1-C4 alkyl; and
wherein at least two of the R2 and R3 groups in said compound are C1-C4 alkyl when Y is not a phenyl moiety, and at least one Y is —
NO2 when Z is alkyl; and
a pharmaceutically-acceptable carrier.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35)
- NO2, and the phenyl moiety
-
22. A pharmaceutical compound comprising a safe and effective amount of a compound selected from
wherein R5 and R6 are selected from the following moiety pairs CH3, CH3; - Ph, H and H, Ph;
R7 is selected from H and CH3; and
R8 is selected from O, S, NH and NCH3; and
a pharmaceutically-acceptable carrier.
- Ph, H and H, Ph;
-
36. The compound having the formula
wherein R2 is selected from the group consisting of H, C1-C4 alkyl and C1-C4 substituted alkyl.
-
39. A pharmaceutical composition comprising a safe and effective amount of a compound selected from
wherein Y is selected form the group consisting of H, C1-C4 alkyl, C1-C4 substituted alkyl, — - NO2, and the phenyl moiety
and wherein no more than one Y group is said active compound may be the phenyl moiety;
R1 is selected from the group consisting H, —
OH, halogens, C1-C4 alkyl, C1-C4 substituted alkyl, C1-C4 ester and C1-C4 substituted ester;
R2 is selected from the group consisting of H, C1-C4 alkyl and C1-C4 substituted alkyl;
R3 is selected from the group consisting of H, C1-C4 alkyl, C1-C4 substituted alkyl, and —
CH2Ph;
R4 is selected from the group consisting of H, C1-C4 alkyl and C1-C4 substituted alkyl;
X is selected from S and O;
Z is selected from —
SR3, —
OR3, —
S(O)R3, —
SR3, and C1-C4 alkyl; and
wherein at least two of the R2 and R3 groups in said compound are C1-C4 alkyl when Y is not a phenyl moiety, and at least one Y is —
NO2, when Z is alkyl; and
a pharmaceutically-acceptable carrier.- View Dependent Claims (40, 41, 42, 43, 44)
wherein R9 is selected from the group consisting of — - OH, —
M and —
OOCCH2M;
wherein M is selected from F, Cl, Br and I.
-
41. A pharmaceutical composition according to claim 39 wherein the active compound is selected from the group consisting of
wherein R10 is selected from the group consisting of H, — - NO2, Ph, 4-HOPh and 4-MPh, wherein M is selected from F, Cl, Br and I.
-
42. A method of treating autoimmune diseases in a patient in need of such treatment by administering to that patient a safe and effective amount of the pharmaceutical composition accord to claim 39.
-
43. A method of treating autoimmune disease in a patient in need of such treatment by administering to that patient a safe and effective amount of the pharmaceutical composition according to claim 40.
-
44. A method of treating autoimmune diseases in a patient in need of such treatment by administering to that patient a safe and effective amount of the pharmaceutical composition according to claim 41.
- NO2, and the phenyl moiety
Specification
-
- Resources
Litigation Campaign Assessment
Thank you for your request. You will receive a custom alert email when the Litigation Campaign Assessment is available.
×
-
Current AssigneeSenco Brands Incorporated (Kyocera Corporation), The United States of America As Represented By The Secretary of Agriculture
-
Original AssigneeSentron Medical, Inc., United States Department Of Health And Human Services
-
InventorsKohn, Leonard D., Rice, John M., Curley, Robert W.
-
Primary Examiner(s)CRIARES, THEODORE J
-
Application NumberUS09/382,960Time in Patent Office951 DaysField of Search514/396, 514/398US Class Current514/396CPC Class CodesA61K 31/4164 1,3-DiazolesA61K 31/4166 having oxo groups directly ...A61K 31/421 1,3-Oxazoles, e.g. pemoline...A61K 31/426 1,3-ThiazolesA61P 1/04 for ulcers, gastritis or re...A61P 1/14 Prodigestives, e.g. acids, ...A61P 1/16 for liver or gallbladder di...A61P 11/06 AntiasthmaticsA61P 13/02 of urine or of the urinary ...A61P 13/12 of the kidneysA61P 15/10 for impotenceA61P 17/00 Drugs for dermatological di...A61P 17/02 for treating wounds, ulcers...A61P 17/06 AntipsoriaticsA61P 17/14 for baldness or alopeciaA61P 19/02 for joint disorders, e.g. a...A61P 21/00 Drugs for disorders of the ...A61P 21/04 for myasthenia gravisA61P 25/00 Drugs for disorders of the ...A61P 27/16 OtologicalsView All
