You’re using a public version of DrugPatentWatch with 5 free searches available | Register to unlock more free searches. CREATE FREE ACCOUNT

Last Updated: March 28, 2024

Claims for Patent: RE43833


✉ Email this page to a colleague

« Back to Dashboard


Summary for Patent: RE43833
Title:Thiazolidin-4-one derivatives
Abstract: The invention relates to pharmaceutical compositions containing at least one thiazolidin-4-one derivative to prevent or treat disorders associated with an activated immune system. Furthermore, the invention relates to novel thiazolidin-4-one derivatives notably for use as pharmaceutically active compounds. Said compounds particularly act also as immunosuppressive agents.
Inventor(s): Binkert; Christoph (Basel, CH), Bolli; Martin (Allschwil, CH), Mathys; Boris (Egerkingen, CH), Mueller; Claus (Weil am Rhein, DE), Scherz; Michael (Ettingen, CH), Nayler; Oliver (Arlesheim, CH)
Assignee: Actelion Pharmaceuticals Ltd. (Allschwil, CH)
Application Number:13/205,768
Patent Claims:1. A pharmaceutical composition containing at least one thiazolidin-4-one derivative of the Formula (I) ##STR00236## wherein: R.sup.1 represents lower alkyl, lower alkenyl; cycloalkyl; 5,6,7,8-tetrahydronaphth-1-yl; 5,6,7,8-tetrahydronaphth-2-yl; or an unsubstituted phenyl group; R.sup.2 represents lower alkyl; allyl; cyclopropyl; cyclobutyl; cyclopentyl; or mono- or di-lower alkylamino; R.sup.3 represents --O--CR.sup.7R.sup.8--CR.sup.9R.sup.10--(CR.sup.11R.sup.12).sub.n--O--R.s- up.13; R.sup.4 represents hydrogen; hydroxy; lower alkoxy; lower alkyl; or halogen; R.sup.5 and R.sup.6 each represents independently lower alkyl; R.sup.7 represents hydrogen, lower alkyl, or hydroxymethyl; R.sup.8, R.sup.9, R.sup.11 and R.sup.12 each represents independently hydrogen or methyl; R.sup.10 represents hydrogen or lower alkyl; in case n represents the integer 1, R.sup.10 in addition represents lower alkoxy, hydroxy, --NH.sub.2, --NHR.sup.5 or --NR.sup.5R.sup.6; R.sup.13 represents hydrogen; lower alkyl; hydroxycarbonyl-lower alkyl; 1-glyceryl or 2-glyceryl; n represents the integer 0 or 1; in a configurational isomeric, an optically pure enantiomeric, a mixture of enantiomeric, an enantiomeric racemate, a diastereomeric, a mixture of diastereomeric, a diastereomeric racemate, a mixture of diastereomeric racemates, a meso-form, free or pharmaceutically acceptable salt form, and an inert carrier material.

2. The pharmaceutical composition according to claim 1, in which said thiazolidin-4-one derivatives is a (Z,Z)-isomer.

3. The pharmaceutical composition of claim 1, further comprising one or more immunosuppressant compounds.

4. The pharmaceutical composition according to claim 3, wherein said immunosuppressant compound is selected from the group consisting of cyclosporin, daclizumab, basiliximab, everolimus, tacrolimus (FK506), azathiopirene, leflunomide, and 15-deoxyspergualin.

5. A thiazolidin-4-one derivative of Formula (II) ##STR00237## wherein: R.sup.14 represents lower alkyl, lower alkenyl; cycloalkyl; 5,6,7,8-tetrahydronaphth-1-yl; 5,6,7,8-tetrahydronaphth-2-yl; or an unsubstituted phenyl group; R.sup.15 represents lower alkyl; allyl; cyclopropyl; cyclobutyl; cyclopentyl; or mono- or di-lower alkylamino; R.sup.16 represents hydrogen; hydroxy; lower alkoxy; lower alkyl or halogen; R.sup.17 represents hydrogen, lower alkyl, or hydroxymethyl; R.sup.18, R.sup.19, R.sup.21 and R.sup.22 each represents independently hydrogen or methyl; R.sup.20 represents hydrogen or lower alkyl; and in case m represents the integer 1, R.sup.20 in addition represents lower alkoxy, hydroxy, --NH.sub.2, --NHR.sup.5 or --NR.sup.5R.sup.6; R.sup.23 represents hydrogen; lower alkyl; hydroxycarbonyl-lower alkyl; 1-glyceryl or 2-glyceryl; R.sup.5 and R.sup.6 each represents independently lower alkyl; m represents the integer 0 or 1; in a configurational isomeric, an optically pure enantiomeric, a mixture of enantiomeric, an enantiomeric racemate, a diastereomeric, a mixture of diastereomeric, a diastereomeric racemate, a mixture of diastereomeric racemates, a meso-form, a free or a pharmaceutically acceptable salt form.

6. The thiazolidin-4-one derivative according to claim 5 in which said thiazolidin-4-one derivative according to formula (II) is a (Z,Z) isomer.

7. The thiazolidin-4-one derivative according to claim 5 or 6, wherein R.sup.14 represents an unsubstituted phenyl group.

8. The thiazolidin-4-one derivative according to claim 5 or 6, wherein R.sup.15 represents lower alkyl.

9. The thiazolidin-4-one derivative according to claim 5 or 6, wherein R.sup.16 represents halogen or methyl.

10. The thiazolidin-4-one derivative according to claim 5 or 6, wherein m represents the integer 0, and R.sup.17, R.sup.18, R.sup.19 and R.sup.20 represent hydrogen.

11. The thiazolidin-4-one derivative according to claim 5 or 6, wherein m represents the integer 1, R.sup.17, R.sup.18, R.sup.19, R.sup.21 and R.sup.22 represent hydrogen, and R.sup.20 represents hydroxy.

12. The thiazolidin-4-one derivative according to claim 5 or 6, wherein R.sup.23 represents hydrogen.

13. The thiazolidin-4-one derivative according to claim 5 or 6, wherein m represents the integer 0, and R.sup.17, R.sup.18, R.sup.19, R.sup.20 and R.sup.23 represent hydrogen.

14. The thiazolidin-4-one derivative according to claim 5 or 6, wherein m represents the integer 1, R.sup.17, R.sup.18, R.sup.19, R.sup.21, R.sup.22 and R.sup.23 represent hydrogen, and R.sup.20 represents hydroxy.

15. The thiazolidin-4-one derivative according to claim 5 or 6, wherein R.sup.14 represents an unsubstituted phenyl group, and R.sup.15 represents lower alkyl.

16. The thiazolidin-4-one derivative according to claim 5 or 6, wherein R.sup.14 represents an unsubstituted phenyl group, m represents the integer 0, and R.sup.17, R.sup.18, R.sup.19, R.sup.20 and R.sup.23 represent hydrogen.

17. The thiazolidin-4-one derivative according to claim 5 or 6, wherein R.sup.14 represents an unsubstituted phenyl group, m represents the integer 1, R.sup.17, R.sup.18, R.sup.19, R.sup.21, R.sup.22 and R.sup.23 represent hydrogen, and R.sup.20 represents hydroxy.

18. The thiazolidin-4-one derivative according to claim 5 or 6, wherein R.sup.14 represents an unsubstituted phenyl group, R.sup.15 represents lower alkyl, R.sup.16 represents methyl or halogen, m represents the integer 0, and R.sup.17, R.sup.18, R.sup.19, R.sup.20 and R.sup.23 each represent hydrogen.

19. The thiazolidin-4-one derivative according to claim 5 or 6, wherein R.sup.14 represents an unsubstituted phenyl group, R.sup.15 represents lower alkyl, R.sup.16 represents methyl or halogen, m represents the integer 1, R.sup.17, R.sup.18, R.sup.19, R.sup.21, R.sup.22 and R.sup.23 represent hydrogen, and R.sup.20 represents hydroxy.

20. The thiazolidin-4-one derivative according to claim 5 selected from the group consisting of: 5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-isopropylimino)-3-phenyl-t- hiazolidin-4-one, {2-[4-(2-([Z]-isopropylimino)-4-oxo-3-phenyl-thiazolidin-5-[Z]-ylidenemet- hyl)-phenoxy]-ethoxy}-acetic acid, 5-{4-[2-(2,3-dihydroxy-propoxy)-ethoxy]-benz[Z]ylidene}-2-([Z]-isopropyli- mino)-3-phenyl-thiazolidin-4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-isopropylimino)-3- -phenyl-thiazolidin-4-one, 5-[3-fluoro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-isopropylimino)-3- -phenyl-thiazolidin-4-one, 5-[4-(2-hydroxy-ethoxy)-3-methyl-benz[Z]ylidene]-2-([Z]-isopropylimino)-3- -phenyl-thiazolidin-4-one, 5-[4-(2-hydroxy-ethoxy)-3-methoxy-benz[Z]ylidene]-2-([Z]-isopropylimino)-- 3-phenyl-thiazolidin-4-one, 5-[4-(3-hydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-isopropylimino)-3-phenyl-- thiazolidin-4-one, 5-[4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-isopropylimino)-3-phe- nyl-thiazolidin-4-one, 5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-isopropylimi- no)-3-phenyl-thiazolidin-4-one, 3-allyl-5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-isopropylimino)-th- iazolidin-4-one, 3-allyl-5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-isopropyl- imino)-thiazolidin-4-one, 3-allyl-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-isop- ropylimino)-thiazolidin-4-one, 5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phenyl-2-([Z]-propylimino)-thia- zolidin-4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phenyl-2-([Z]-propylim- ino)-thiazolidin-4-one, 5-[4-(2-hydroxy-ethoxy)-3-methyl-benz[Z]ylidene]-3-phenyl-2-([Z]-propylim- ino)-thiazolidin-4-one, 5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-3-phenyl-2-([Z]-pro- pylimino)-thiazolidin-4-one, 2-([Z]-tert-butylimino)-5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-- 3-phenyl-thiazolidin-4-one, 2-(dimethyl-hydrazono)-5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phenyl-t- hiazolidin-4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-(dimethyl-hydrazono)-3- -phenyl-thiazolidin-4-one, 2-([Z]-ethylimino)-5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phenyl-thiaz- olidin-4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-ethylimino)-3-phe- nyl-thiazolidin-4-one, 2-([Z]-butylimino)-5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phenyl-thiaz- olidin-4-one, 2-([Z]-butylimino)-5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phe- nyl-thiazolidin-4-one, 2-([Z]-sec-butylimino)-5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3- -phenyl-thiazolidin-4-one, 2-([Z]-cyclopropylimino)-5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phenyl- -thiazolidin-4-one, 3-cyclohexyl-5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-isopropylimin- o)-thiazolidin-4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-cyclohexyl-2-([Z]-isop- ropylimino)-thiazolidin-4-one, 5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-isopropyl-2-([Z]-isopropylimino- )-thiazolidin-4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-isopropyl-2-([Z]-isopr- opylimino)-thiazolidin-4-one, 5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-3-isopropyl-2-([Z]-- isopropylimino)-thiazolidin-4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-isopropylimino)-3- -phenyl-thiazolidin-4-one, 2-([Z]-allylimino)-5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phenyl-thiaz- olidin-4-one, 2-([Z]-allylimino)-5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phe- nyl-thiazolidin-4-one, 3-allyl-2-([Z]-allylimino)-5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-thiazo- lidin-4-one, 3-allyl-2-([Z]-allylimino)-5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]yliden- e]-thiazolidin-4-one, and 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-methylimino)-3-ph- enyl-thiazolidin-4-one.

21. The thiazolidin-4-one derivative according to claim 5 selected from the group consisting of: 5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-isopropylimino)-3-phenyl-t- hiazolidin-4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-isopropylimino)-3- -phenyl-thiazolidin -4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phenyl-2-([Z]-propylim- ino)-thiazolidin-4-one, 5-[4-(2-hydroxy-ethoxy)-3-methyl-benz[Z]ylidene]-3-phenyl-2-([Z]-propylim- ino)-thiazolidin-4-one, 5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-3-phenyl-2-([Z]-pro- pylimino)-thiazolidin-4-one, 2-(dimethyl-hydrazono)-5-[4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-phenyl-t- hiazolidin-4-one, 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-2-([Z]-ethylimino)-3-phe- nyl-thiazolidin -4-one, and 5-[3-chloro-4-(2-hydroxy-ethoxy)-benz[Z]ylidene]-3-isopropyl-2-([Z]-isopr- opylimino)-thiazolidin-4-one.

22. A pharmaceutical composition comprising at least one thiazolidin-4-one derivative of claim 5 and inert carrier material.

23. A process for the preparation of a pharmaceutical composition comprising mixing one or more thiazolidin-4-one derivatives of any one of claim 5, 20 or 21 with an inert excipient.

24. A process for the preparation of the pharmaceutical composition of claim 1, comprising mixing one or more thiazolidin-4-one derivatives according to claim 1 with an inert excipient.

Details for Patent RE43833

Applicant Tradename Biologic Ingredient Dosage Form BLA Approval Date Patent No. Expiredate
Hoffmann-la Roche Inc. ZENAPAX daclizumab Injection 103749 12/10/1997 ⤷  Try a Trial 2023-11-21
Novartis Pharmaceuticals Corporation SIMULECT basiliximab For Injection 103764 05/12/1998 ⤷  Try a Trial 2023-11-21
Novartis Pharmaceuticals Corporation SIMULECT basiliximab For Injection 103764 01/02/2003 ⤷  Try a Trial 2023-11-21
Biogen Inc. ZINBRYTA daclizumab Injection 761029 05/27/2016 ⤷  Try a Trial 2023-11-21
Biogen Inc. ZINBRYTA daclizumab Injection 761029 05/26/2017 ⤷  Try a Trial 2023-11-21
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Approval Date >Patent No. >Expiredate

Make Better Decisions: Try a trial or see plans & pricing

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.