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Last Updated: July 8, 2020

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Claims for Patent: 7,435,750

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Summary for Patent: 7,435,750
Title:Method of using substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
Abstract: The present invention is directed to substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs thereof, represented by the Formula I: ##STR00001## wherein Ar.sub.1, Ar.sub.3, A, B and D are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.
Inventor(s): Cai; Sui Xiong (San Diego, CA), Zhang; Han-Zhong (San Diego, CA), Drewe; John A. (Carlsbad, CA), Reddy; P. Sanjeeva (San Diego, CA), Kasibhatla; Shailaja (San Diego, CA), Kuemmerle; Jared Daniel (Del Mar, CA), Ollis; Kristin P. (San Diego, CA)
Assignee: Cytovia, Inc. (San Diego, CA)
Application Number:11/074,077
Patent Claims:1. A method of treating breast cancer or colon carcinoma in an animal suffering therefrom, comprising administering to an animal in need of such treatment an effective amount of a compound having the Formula II: ##STR00019## or a pharmaceutically acceptable salt or prodrug or tautomers thereof, wherein: Ar.sub.1 is optionally substituted heteroaryl; and Ar.sub.3 is optionally substituted and selected from the group consisting of pyridyl, quinolyl, isoquinolyl, isoxazolyl, pyrazolyl, imidazolyl, thienyl, furyl, pyrrolyl and pyrazolo[1,5.alpha.]pyrimidinyl.

2. The method of claim 1, wherein Ar.sub.1 is pyridyl, quinolyl, isoquinolyl, isoxazolyl, pyrazolyl, imidazolyl, thienyl, furyl or pyrrolyl, each of which is optionally substituted.

3. The method of claim 1, wherein Ar.sub.1 is isoxazolyl, pyrazolyl, imidazolyl, thienyl, furyl or pyrrolyl, each of which is optionally substituted; and Ar.sub.3 is optionally substituted pyridyl.

4. The method of claim 1, wherein said compound is selected from the group consisting of: 5-(4-Bromo-1-ethyl-3-methyl-1H-pyrazol-5-yl)-3-(5-trifluoromethyl-pyridin- -2-yl)-[1,2,4]-oxadiazole; 5-(2-Methyl-pyrrol-3-yl)-3-(pyridin-3-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(pyridin-4-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(pyridin-3-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(pyridin-2-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(N-oxide-pyridin-4-yl)-[1,2,4]-oxadiazole; 5-(3-Methyl-furan-2-yl)-3-(5-trifluoromethyl-pyridin-2-yl)-[1,2,4]-oxadia- zole; 5-(4-Chloro-1H-pyrazol-3-yl)-3-(5-trifluoromethyl-pyridin-2-yl)-[1,2- ,4]-oxadiazole; 5-(3-Chloro-furan-2-yl)-3-(5-trifluoromethyl-pyridin-2-yl)-[1,2,4]-oxadia- zole; 5-(4-Chloro-thiazol-5-yl)-3-(5-chloro-pyridin-2-yl)-[1,2,4]-oxadiazo- le; 5-(3-Chloro-thiophen-2-yl)-3-(5-chloro-pyridin-2-yl)-[1,2,4]-oxadiazol- e; 5-(3-Chloro-thiophen-2-yl)-3-(5-trifluoromethyl-pyridin-2-yl)-[1,2,4]-o- xadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(N-oxide-pyridin-3-yl)-[1,2,4]-oxa- diazole; 5-(3-Chloro-thiophen-2-yl)-3-(6-chloro-pyridin-3-yl)-[1,2,4]-oxad- iazole; 5-(3-Chloro-thiophen-2-yl)-3-(5-trifluoromethyl-pyridin-2-yl)-[1,2- ,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(6-trifluoromethyl-pyridin-3-yl)-[1,2,4]-oxa- diazole; 5-(3-Chloro-thiophen-2-yl)-3-(quinoline-2-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(isoquinoline-3-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(4-methyl-pyridin-2-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(4-cyano-pyridin-2-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(5-methyl-pyridin-2-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(6-methyl-pyridin-3-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(pyrazin-2-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(quinolin-3-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-thiophen-2-yl)-3-(8-hydroxy-quinolin-2-yl)-[1,2,4]-oxadiazole- ; 5-(3-Cyano-thiophen-2-yl)-3-(5-trifluoromethyl-pyridin-2-yl)-[1,2,4]-oxa- diazole; 5-(3-Chloro-thiophen-2-yl)-3-(5,6-dichloro-pyridin-3-yl)-[1,2,4]-- oxadiazole; 5-(3-Bromo-furan-2-yl)-3-(5-chloro-pyridin-2-yl)-[1,2,4]-oxadiazole; 5-(3-Bromo-furan-2-yl)-3-(6-trifluoromethyl-pyridin-3-yl)-[1,2,4]-oxadiaz- ole; 5-(3-Bromo-furan-2-yl)-3-(5-trifluoromethyl-pyridin-2-yl)-[1,2,4]-oxa- diazole; 5-(3-Chloro-thiophen-2-yl)-3-(7-methyl-5-trifluoromethyl-pyrazolo [1,5-.alpha.]pyrimidin-3-yl)-[1,2,4]-oxadiazole; 5-(3-Chloro-furan-2-yl)-3-(5-chloro-pyridin-2-yl)-[1,2,4]-oxadiazole; 5-(3-Bromo-furan-2-yl)-3-(5-trifluoromethyl-pyridin-2-yl)-[1,2,4]-oxadiaz- ole; 5-(3-Bromo-furan-2-yl)-3-(5-chloro-pyridin-2-yl)-[1,2,4]-oxadiazole; and 5-(3-Chloro-thiophen-2-yl)-3-(6-methoxy-pyridin-3-yl)-[1,2,4]-oxadiaz- ole; or a pharmaceutically acceptable salt or prodrug thereof.

5. The method of claim 1, wherein said animal is a mammal.

6. The method of claim 1 additionally comprising administering at least one known cancer chemotherapeutic agent, or a pharmaceutically acceptable salt of said agent.

7. The method of claim 6, wherein said known cancer therapeutic agent is selected from the group consisting of busulfan, cis-platin, mitomycin C, carboplatin, colchicine, vinblastine, paclitaxel, docetaxel, camptothecin, topotecan, doxorubicin, etopo side, 5-azacytidine, 5-fluorouracil, methotrexate, 5-fluoro-2'-deoxy-uridine, ara-C, hydroxyurea, thioguanine, melphalan, chlorambucil, cyclophosamide, ifosfamide, vincristine, mitoguazone, epirubicin, aclarubicin, bleomycin, mitoxantrone, elliptinium, fludarabine, octreotide, retinoic acid, tamoxifen, campath, imatinib, trastuzumab or rituximab and alanosine.

8. The method of claim 1 additionally comprising treating said animal with radiation-therapy.

9. The method of claim 1 wherein said compound is administered after surgical treatment of said animal for said cancer.

10. The method of claim 1, wherein Ar.sub.2 is pyridyl, which is optionally substituted.

11. The method of claim 1 wherein the disease is breast cancer.

12. The method of claim 1 wherein the disease is colon carcinoma.

Details for Patent 7,435,750

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Genentech RITUXAN rituximab SOLUTION;INTRAVENOUS 103705 001 1997-11-26   Start Trial Cytovia, Inc. (San Diego, CA) 2039-03-29 RX search
Genentech RITUXAN rituximab SOLUTION;INTRAVENOUS 103705 002 1997-11-26   Start Trial Cytovia, Inc. (San Diego, CA) 2039-03-29 RX search
Genentech HERCEPTIN trastuzumab VIAL; INTRAVENOUS 103792 001 1998-09-25   Start Trial Cytovia, Inc. (San Diego, CA) 2039-03-29 RX Orphan search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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