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Last Updated: March 29, 2024

Claims for Patent: 10,434,195


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Summary for Patent: 10,434,195
Title:Methylsulfonamide derivatives and uses related thereto
Abstract: This disclosure relates to methylsulfonamide derivatives and uses as imaging agents and other uses related to CXCR4 inhibition. In certain embodiments, the disclosure relates to pharmaceutical compositions comprising compounds disclosed herein, derivatives, or pharmaceutically acceptable salts or prodrugs thereof. In certain embodiments, the compositions disclosed herein are used for imaging to study CXCR4 related conditions.
Inventor(s): Shim; Hyunsuk (Atlanta, GA), Goodman; Mark M. (Atlanta, GA), Shetty; Dinesh (Atlanta, GA), Oum; Hyeun Yoon (Atlanta, GA)
Assignee: Emory University (Atlanta, GA)
Application Number:15/750,086
Patent Claims:1. A compound having formula ID, ##STR00029## or salts thereof, wherein the compound of formula ID comprises a radionuclide selected from the group consisting of .sup.11C, .sup.13N, .sup.18F, .sup.76Br, .sup.123I, .sup.124I, .sup.125I, and .sup.131I; and wherein, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are each individually and independently hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6, are optionally substituted with one or more, the same or different, R.sup.10; R.sup.20, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 are each individually and independently hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.20, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 are a radionuclide or optionally substituted with a radionuclide, or optionally substituted with R.sup.30,_wherein R.sup.30 is a radionuclide or R.sup.30 is substituted with a radionuclide; L.sup.2 is a linking group comprising one or more bridging groups selected from --[CH.sub.2]--, --[CH.sub.2CH.sub.2]--, --[CH.dbd.CH]--, --O--, --NH--, --S--, --C(O)--, --S(O)--, and --S(O).sub.2--; R.sup.1 is hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.1 is optionally substituted with one or more, the same or different, R.sup.10; R.sup.10 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.10 is optionally substituted with one or more, the same or different, R.sup.11; R.sup.11 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.11 is optionally substituted with one or more, the same or different, R.sup.12; R.sup.12 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methyl sulfinyl, ethyl sulfinyl, mesyl, ethyl sulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N-methyl-N-ethylsulfamoyl, carbocyclyl, aryl, or heterocyclyl; R.sup.30 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.30 is optionally substituted with one or more, the same or different, R.sup.31; R.sup.31 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.31 is optionally substituted with one or more, the same or different, R.sup.32; and R.sup.32 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methyl sulfinyl, ethyl sulfinyl, mesyl, ethyl sulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N-methyl-N-ethylsulfamoyl, carbocyclyl, aryl, or heterocyclyl.

2. The compound of claim 1, wherein R.sup.22 is alkoxy terminally substituted with a radionuclide.

3. A compound having formula IF, ##STR00030## or salts thereof wherein, R.sup.2, R.sup.3, R.sup.5, and R.sup.6 are each individually and independently hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.2, R.sup.3, R.sup.5, and R.sup.6, are optionally substituted with one or more, the same or different, R.sub.10; R.sup.7 and R.sup.8 form a heterocyclyl optionally substituted with one or more, the same or different, R.sup.10; or R.sup.7 and R.sup.8 are each individually and independently hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.7 and R.sup.8, are optionally substituted with one or more, the same or different R.sup.10; R.sup.20, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 are each individually and independently hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.20, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 are a radionuclide or optionally substituted with a radionuclide, or optionally substituted with R.sub.30, wherein R.sup.30 is a radionuclide or R.sup.30 is substituted with a radionuclide; L.sup.2 is a linking group comprising one or more bridging groups selected from --[CH.sub.2]--, --[CH.sub.2CH.sub.2]--, --[CH.dbd.CH]--, --O--, --NH--, --S--, --C(O)--, --S(O)--, and --S(O).sub.2--; R.sup.1 is hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.1 is optionally substituted with R.sup.10; R.sup.10 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.10 is optionally substituted with one or more, the same or different, R.sup.11; R.sup.11 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.11 is optionally substituted with one or more, the same or different, R.sup.12; R.sup.12 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methyl sulfinyl, ethyl sulfinyl, mesyl, ethyl sulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N-methyl-N-ethylsulfamoyl, carbocyclyl, aryl, or heterocyclyl; R.sup.30 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.30 is optionally substituted with one or more, the same or different, R.sup.31; R.sup.31 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.31 is optionally substituted with one or more, the same or different, R.sup.32; and R.sup.32 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methyl sulfinyl, ethyl sulfinyl, mesyl, ethyl sulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N-methyl-N-ethylsulfamoyl, carbocyclyl, aryl, or heterocyclyl.

4. A compound having formula IL, ##STR00031## or salts thereof wherein, r is 1, 2, 3, 4, 5, 6, 7, or 8; V is a radionuclide; R.sup.2, R.sup.3, R.sup.5, and R.sup.6 are each individually and independently hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.2, R.sup.3, R.sup.5, and R.sup.6, are optionally substituted with one or more, the same or different, R.sup.10; R.sup.7 and R.sup.8 form a heterocyclyl optionally substituted with one or more, the same or different, R.sup.10; or R.sup.7 and R.sup.8 are each individually and independently hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.7 and R.sup.8, are optionally substituted with one or more, the same or different R.sup.10; L.sup.2 is a linking group comprising one or more bridging groups selected from --[CH.sub.2]--, --[CH.sub.2CH.sub.2]--, --[CH.dbd.CH]--, --O--, --NH--, --S--, --C(O)--, --S(O)--, and --S(O).sub.2--; R.sup.1 is hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylene glycol, alkanoyl, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.1 is optionally substituted with R.sup.10; R.sup.10 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R.sup.10 is optionally substituted with one or more, the same or different, R.sup.11; R.sup.11 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl).sub.2amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein is optionally substituted with one or more, the same or different, R.sup.12; R.sup.12 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methyl sulfinyl, ethyl sulfinyl, mesyl, ethyl sulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N-methyl-N-ethylsulfamoyl, carbocyclyl, aryl, or heterocyclyl.

5. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable excipient.

6. The pharmaceutical composition of claim 5, further comprising another active agent.

7. A method of scanning a subject for radioactivity emissions comprising a) administering compound comprising a radionuclide according to claim 1 to a subject; and b) scanning the subject for radioactivity emissions.

8. The method of claim 7, further comprising the step of detecting the radioactivity emissions and creating an image indicating the location of the compound comprising the radionuclide in the subject.

9. A method of treating rheumatoid arthritis or psoriatic arthritis comprising administering pharmaceutical composition comprising a compound as described in claim 1 to a subject in need thereof.

10. A method of treating an arthritis comprising administering pharmaceutical composition comprising a compound as described in claim 1 in combination with another active ingredient to a subject in need thereof.

11. The method of claim 10, wherein the other active agent is a non-steroidal anti-inflammatory drugs (NSAIDs), ibuprofen, acetaminophen, methotrexate, abatacept, adalimumab, azathioprine, ciclosporin, rituximab, chloroquine, hydroxychloroquine, etanercept, golimumab, infliximab, leflunomide, minocycline, or combinations thereof.

12. A method of treating cancer comprising administering pharmaceutical composition comprising a compound as described in claim 1 to a subject in need thereof.

13. A pharmaceutical composition comprising a compound according to claim 4 and a pharmaceutically acceptable excipient.

14. The pharmaceutical composition of claim 13, further comprising another active agent.

15. A method of scanning a subject for radioactivity emissions comprising a) administering compound comprising a radionuclide according to claim 4 to a subject; and b) scanning the subject for radioactive emissions.

16. The method of claim 15, further comprising the step of detecting the radioactive emissions and creating an image indicating the location of the compound comprising the radionuclide in the subject.

17. A method of treating rheumatoid arthritis or psoriatic arthritis comprising administering pharmaceutical composition comprising a compound as described in claim 4 to a subject in need thereof.

18. A method of treating an arthritis comprising administering pharmaceutical composition comprising a compound as described in claim 4 in combination with another active ingredient to a subject in need thereof.

19. The method of claim 18, wherein the other active agent is a non-steroidal anti-inflammatory drugs (NSAIDs), ibuprofen, acetaminophen, methotrexate, abatacept, adalimumab, azathioprine, ciclosporin, rituximab, chloroquine, hydroxychloroquine, etanercept, golimumab, infliximab, leflunomide, minocycline, or combinations thereof.

20. A method of treating cancer comprising administering pharmaceutical composition comprising a compound as described in claim 4 to a subject in need thereof.

Details for Patent 10,434,195

Applicant Tradename Biologic Ingredient Dosage Form BLA Approval Date Patent No. Expiredate
Genentech, Inc. RITUXAN rituximab Injection 103705 11/26/1997 ⤷  Try a Trial 2035-08-03
Janssen Biotech, Inc. REMICADE infliximab For Injection 103772 08/24/1998 ⤷  Try a Trial 2035-08-03
Immunex Corporation ENBREL etanercept For Injection 103795 11/02/1998 ⤷  Try a Trial 2035-08-03
Immunex Corporation ENBREL etanercept For Injection 103795 05/27/1999 ⤷  Try a Trial 2035-08-03
Immunex Corporation ENBREL etanercept Injection 103795 09/27/2004 ⤷  Try a Trial 2035-08-03
Immunex Corporation ENBREL etanercept Injection 103795 02/01/2007 ⤷  Try a Trial 2035-08-03
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Approval Date >Patent No. >Expiredate

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