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Claims for Patent: 8,450,377

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Summary for Patent: 8,450,377
Title:1-adamantyl chalcones for the treatment of proliferative disorders
Abstract: The present invention relates to the compounds of the general formula (I), a composition for and a method of treating breast cancer or other proliferative disorders in a subject using a compound of general formula [I], ##STR00001## wherein the substituents are as defined in the specification.
Inventor(s): Anderson; Gloria L. (Atlanta, GA), Kaimari; Tawfeq Abdul-Raheem (Kennesaw, GA)
Assignee:
Application Number:13/224,829
Patent Claims:1. A compound of the formula: ##STR00027## wherein R.sub.1 is Ad- or Ad-(L1)n-, wherein n is 0 or 1, Ad is adamantyl, and L1 is a linking group selected from the group consisting of C1-6 alkylene, C1-6 cycloalkylene, and C1-6 arylene; Y is H; and R.sub.2 is CY1=CHR3, wherein Y1 is H, C1-6 alkyl, aryl, or halo; and R3 is aryl, aryl optionally substituted by X, or HET; X is hydrogen, straight chain or branched C1-6 alkyl, halo, amino, C1-6 alkyl amino, C1-6 dialkyl amino, pyrrolidinyl, piperadinyl, morpholinyl, piperazinyl, C1-6 alkoxy, C1-6 aralkoxyl, aryl, C1-6 aralkyl, nitro, cyano or a phosphorus containing group; and HET is optionally substituted pyrrolidinyl, piperadinyl, morpholinyl, piperazinyl, pyrrolyl, pyridinyl, and pyridazinyl, quinolinyl, or thiophenyl, and wherein the substitutuent is X; or a pharmaceutically acceptable salt or derivative thereof.

2. The compound according to claim 1, having the formula: ##STR00028## wherein R.sub.1 is Ad- or Ad-(L1)n-, wherein n is 0 or 1, Ad is adamantyl, and L1 is a linking group selected from the group consisting of C1-6 alkylene, C1-6 cycloalkylene, and C1-6 arylene; Y is H; R.sub.2 is CY1=CHR3, wherein Y1 is H, C1-6 alkyl, aryl, or halo; R3 is aryl, or aryl optionally substituted by X; and X is hydrogen, straight chain or branched C1-6 alkyl, halo, amino, C1-6 alkyl amino, C1-6 dialkyl amino, pyrrolidinyl, piperadinyl, morpholinyl, piperazinyl, C1-6 alkoxy, C1-6 aralkoxyl, aryl, C1-6 aralkyl, nitro, cyano or a phosphorus containing group; or a pharmaceutically acceptable salt or derivative thereof.

3. The compound according to claim 1 having the formula: ##STR00029## wherein Y is H, C1-6 alkyl, aryl, or halo; and X is hydrogen, straight chain or branched C1-6 alkyl, halo, amino, C1-6 alkyl amino, C1-6 dialkyl amino, pyrrolidinyl, piperadinyl, morpholinyl, piperazinyl, C1-6 alkoxy, C1-6 aralkoxyl, aryl, C1-6 aralkyl, nitro, cyano or a phosphorus containing group; or a pharmaceutically acceptable salt or derivative thereof.

4. The compound according to claim 1 having the formula: ##STR00030## wherein X is H or OCH.sub.3, and Y is H, CH.sub.3 or Cl.

5. A pharmaceutical composition comprising an anti-proliferative effective amount of a compound of claim 1 having the formula: ##STR00031## wherein R.sub.1 is Ad- or Ad-(L1)n-, wherein n is 0 or 1, Ad is adamantyl, and L1 is a linking group selected from the group consisting of C1-6 alkylene, C1-6 cycloalkylene, and C1-6 arylene; Y is H; R.sub.2 is CY1=CHR3, wherein Y1 is H, C1-6 alkyl, aryl, or halo; R3 is aryl, or aryl optionally substituted by X; and X is hydrogen, straight chain or branched C1-6 alkyl, halo, amino, C1-6 alkyl amino, C1-6 dialkyl amino, pyrrolidinyl, piperadinyl, morpholinyl, piperazinyl, C1-6 alkoxy, C1-6 aralkoxyl, aryl, C1-6 aralkyl, nitro, cyano or a phosphorus containing group; or a pharmaceutically acceptable salt or derivative thereof, in combination with a pharmaceutically acceptable carrier.

6. A pharmaceutical composition comprising an anti-proliferative effective amount of a compound of claim 1 having the formula: ##STR00032## wherein Y is H, C1-6 alkyl, aryl, or halo; and X is hydrogen, straight chain or branched C1-6 alkyl, halo, amino, C1-6 alkyl amino, C1-6 dialkyl amino, pyrrolidinyl, piperadinyl, morpholinyl, piperazinyl, C1-6 alkoxy, C1-6 aralkoxyl, aryl, C1-6 aralkyl, nitro, cyano or a phosphorus containing group; or a pharmaceutically acceptable salt or derivative thereof, in combination with a pharmaceutically acceptable carrier.

7. A method for the treatment of breast cancer comprising administering to a host in need of such treatment an anti-proliferative effective amount of a compound according to claim 1 having the formula: ##STR00033## wherein R.sub.1 is Ad- or Ad-(L1)n-, wherein n is 0 or 1, Ad is adamantyl, and L1 is a linking group selected from the group consisting of C1-6 alkylene, C1-6 cycloalkylene, and C1-6 arylene; Y is H; and R.sub.2 is CH.dbd.CHR3, wherein R.sub.3 is aryl, aryl optionally substituted by X, and X is hydrogen, straight chain or branched C1-6 alkyl, halo, amino, C1-6 alkyl amino, C1-6 dialkyl amino, pyrrolidinyl, piperadinyl, morpholinyl, piperazinyl, C1-6 alkoxy, C1-6 aralkoxyl, aryl, C1-6 aralkyl, nitro, cyano or a phosphorus containing group; or a pharmaceutically acceptable salt or derivative thereof in combination with at least one other chemotherapeutic agent selected from the group consisting of tamoxifen, toremifene, idoxifene, droloxifene, TAT-59, LY117018, raloxifene, genistein, doxyrubicin, Taxol, Taxotere, aredia, arimidex, navilbine, busulfan, cisplatin, cyclophosphamide (Cytoxan), dacarbazine, ifosfamide, mechlorethamine (Mustargen), melphalan, carmustine, lomustine, 5-fluorouracil, methotrexate, gemcitabine, cytarabine (Ara-C), fludarabine, bleomycin, dactinomycin, daunorubicin, idarubicin, paclitaxel, docetaxel, etoposide, vinblastine, vincristine, vinorelbine, prednisone, dexamethasone, and herceptin, optionally in combination with a pharmaceutically acceptable carrier.

8. A method for the treatment of breast cancer comprising administering to a host in need of such treatment an effective amount of a compound according to claim 1 having the formula: ##STR00034## wherein R.sub.2 is CH.dbd.CHR3, wherein R3 is aryl, aryl optionally substituted by X, wherein X is hydrogen, straight chain or branched C1-6 alkyl, halo, amino, C1-6 alkyl amino, C1-6 dialkyl amino, pyrrolidinyl, piperadinyl, morpholinyl, piperazinyl, C1-6 alkoxy, C1-6 aralkoxyl, aryl, C1-6 aralkyl, nitro, cyano or a phosphorus containing group; or a pharmaceutically acceptable salt or derivative thereof in combination with at least one other chemotherapeutic agent selected from the group consisting of tamoxifen, toremifene, idoxifene, droloxifene, TAT-59, LY117018, raloxifene, genistein, doxyrubicin, Taxol, Taxotere, aredia, arimidex, navilbine, busulfan, cisplatin, cyclophosphamide (Cytoxan), dacarbazine, ifosfamide, mechlorethamine (Mustargen), melphalan, carmustine, lomustine, 5-fluorouracil, methotrexate, gemcitabine, cytarabine (Ara-C), fludarabine, bleomycin, dactinomycin, daunorubicin, idarubicin, paclitaxel, docetaxel, etoposide, vinblastine, vincristine, vinorelbine, prednisone, dexamethasone, and herceptin, optionally in combination with a pharmaceutically acceptable carrier.

9. A method for the treatment of breast cancer comprising administering to a host in need of such treatment an effective amount of a compound according to claim 1 having the formula: ##STR00035## wherein X is H or OCH.sub.3, and Y is H, CH.sub.3 or Cl; or a pharmaceutically acceptable salt or derivative thereof in combination with at least one other chemotherapeutic agent selected from the group consisting of tamoxifen, toremifene, idoxifene, droloxifene, TAT-59, LY117018, raloxifene, genistein, doxyrubicin, Taxol, Taxotere, aredia, arimidex, navilbine, busulfan, cisplatin, cyclophosphamide (Cytoxan), dacarbazine, ifosfamide, mechlorethamine (Mustargen), melphalan, carmustine, lomustine, 5-fluorouracil, methotrexate, gemcitabine, cytarabine (Ara-C), fludarabine, bleomycin, dactinomycin, daunorubicin, idarubicin, paclitaxel, docetaxel, etoposide, vinblastine, vincristine, vinorelbine, prednisone, dexamethasone, and herceptin, optionally in combination with a pharmaceutically acceptable carrier.

Details for Patent 8,450,377

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Genentech HERCEPTIN trastuzumab VIAL; INTRAVENOUS 103792 001 1998-09-25   Start Trial 2039-02-26 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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