US2020268714A1PendingUtilityA1

Spirocyclic compounds

63
Assignee: RECURIUM IP HOLDINGS LLCPriority: Apr 3, 2015Filed: Jan 6, 2020Published: Aug 27, 2020
Est. expiryApr 3, 2035(~8.7 yrs left)· nominal 20-yr term from priority
C07D 487/10C07D 471/10A61K 31/5377A61K 31/506A61K 31/496A61K 31/4545A61K 31/444A61K 31/4439A61P 35/00A61K 31/416A61K 31/4162
63
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Claims

Abstract

Disclosed herein are spirocyclic compounds, together with pharmaceutical compositions and methods of ameliorating and/or treating a cancer described herein with one or more of the compounds described herein.

Claims

exact text as granted — not AI-modified
1 . A compound of Formula (I): 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is selected from the group consisting of hydrogen, an unsubstituted C 1-6  alkyl, an unsubstituted or a substituted monocyclic C 3-8  cycloalkyl, an unsubstituted or a substituted phenyl, an unsubstituted or a substituted 5- to 10-membered monocyclic or bicyclic heteroaryl, an unsubstituted or a substituted 5- to 10-membered monocyclic heterocyclyl, cyano, an unsubstituted C 1-6  haloalkyl, amino, a mono-C 1-6  alkyl substituted amino group and a di-C 1-6  alkyl substituted amino group; 
         Y 1  is C or N,
 provided that when Y 1  is C, then R 2a  is selected from the group consisting of hydrogen, halogen, an unsubstituted C 1-6  alkyl, hydroxy, an unsubstituted C 1-6  alkoxy, cyano, nitro and amino, and when Y 1  is N, then R 2a  is absent; 
 
         Y 2  is C, and R 2b  is selected from the group consisting of hydrogen, halogen, an unsubstituted C 1-6  alkyl, hydroxy, an unsubstituted C 1-6  alkoxy, cyano, nitro and amino; 
         Y 3  is C, and R 2c  is selected from the group consisting of hydrogen, halogen, an unsubstituted C 1-6  alkyl, hydroxy, an unsubstituted C 1-6  alkoxy, cyano, nitro and amino; 
         each R 3a , each R 3b , R 3c , R 3d , each R 3e , each R 3f , R 3g , R 3h , R 3i  and R 3j  are independently selected from the group consisting of hydrogen, halogen, an unsubstituted alkyl, hydroxy, an unsubstituted alkoxy and amino; 
         each R 4a  and each R 4b  are independently hydrogen or deuterium; 
         R 5a , R 5b , R 5c , R 5e , R 5f , R 5g  and R 5h  are independently selected from the group consisting of hydrogen and an unsubstituted alkyl; 
         R 6  is an unsubstituted or a substituted phenyl, an unsubstituted or a substituted 5- to 6-membered monocyclic heteroaryl or an unsubstituted or a substituted 5- to 6-membered monocyclic heterocyclyl; 
         A 1  is selected from the group consisting of an unsubstituted bridged C 3-10  cycloalkyl, an unsubstituted or a substituted phenyl and an unsubstituted or a substituted monocyclic heteroaryl; 
         X 1  is hydrogen, O or S, provided that when X 1  is hydrogen, then ------- is a single bond, and when X 1  is O or S, then ------- is a double bond; 
         X 2  is O or S; 
         Y 4  is C(Y 1a ), C or N, 
         Y 1a  is selected from the group consisting of hydrogen, halogen, an unsubstituted C 1-4  alkyl and —O—C 1-4  alkyl; 
            is a single or double bond; 
         wherein when Y 4  is C(Y 1a ) and   is a single bond, then R 5d  is selected from the group consisting of hydrogen and an unsubstituted alkyl; 
         wherein when Y 4  is C and   is a double bond, then R 5d  is absent; and 
         wherein when Y 4  is N, then   is a single bond and R 5d  is selected from the group consisting of hydrogen and an unsubstituted alkyl; 
         m is 1 or 2; 
         n is 1 or 2; and 
         p is 1. 
       
     
     
         2 . (canceled) 
     
     
         3 . The compound of  claim 1 , wherein m is 1; n is 1; and each R 3a , each R 3b , R 3c , R 3d , each R 3e , each R 3f , R 3g , R 3h , R 3i  and R 3j  are each hydrogen. 
     
     
         4 . (canceled) 
     
     
         5 . (canceled) 
     
     
         6 . (canceled) 
     
     
         7 . (canceled) 
     
     
         8 . (canceled) 
     
     
         9 . The compound of  claim 3 , wherein X 1  is hydrogen, and ------- is a single bond. 
     
     
         10 . The compound of  claim 3 , wherein X 1  is O, and ------- is a double bond. 
     
     
         11 . (canceled) 
     
     
         12 . (canceled) 
     
     
         13 . (canceled) 
     
     
         14 . (canceled) 
     
     
         15 . (canceled) 
     
     
         16 . (canceled) 
     
     
         17 . (canceled) 
     
     
         18 . (canceled) 
     
     
         19 . (canceled) 
     
     
         20 . (canceled) 
     
     
         21 . (canceled) 
     
     
         22 . (canceled) 
     
     
         23 . (canceled) 
     
     
         24 . (canceled) 
     
     
         25 . (canceled) 
     
     
         26 . (canceled) 
     
     
         27 . (canceled) 
     
     
         28 . (canceled) 
     
     
         29 . The compound of  claim 10 , wherein Y 1  is C; R 2a  is hydrogen; Y 2  is C; R 2b  is hydrogen; Y 3  is C; R 2c  is hydrogen. 
     
     
         30 . (canceled) 
     
     
         31 . (canceled) 
     
     
         32 . (canceled) 
     
     
         33 . The compound of  claim 10 , wherein Y 1  is N; R 2a  is absent; Y 2  is C; R 2b  is hydrogen; Y 3  is C; R 2c  is hydrogen. 
     
     
         34 . (canceled) 
     
     
         35 . (canceled) 
     
     
         36 . (canceled) 
     
     
         37 . (canceled) 
     
     
         38 . (canceled) 
     
     
         39 . (canceled) 
     
     
         40 . (canceled) 
     
     
         41 . (canceled) 
     
     
         42 . (canceled) 
     
     
         43 . (canceled) 
     
     
         44 . (canceled) 
     
     
         45 . (canceled) 
     
     
         46 . (canceled) 
     
     
         47 . The compound of  claim 29 , wherein each R 4a  and each R 4b  are each hydrogen; and X 2  is O. 
     
     
         48 . (canceled) 
     
     
         49 . (canceled) 
     
     
         50 . (canceled) 
     
     
         51 . The compound of  claim 47 , wherein Y 4  is C(Y 1a );   is a single bond; and R 5a , R 5b , R 5c , R 5d , R 5e , R 5f , R 5g  and R 5h  are each hydrogen. 
     
     
         52 . (canceled) 
     
     
         53 . The compound of  claim 47 , wherein Y 4  is C;   is a double bond; R 5d  is absent; and R 5a , R 5b , R 5c , R 5e , R 5f , R 5g  and R 5h  are each hydrogen. 
     
     
         54 . (canceled) 
     
     
         55 . The compound of  claim 47 , wherein Y 4  is N;   is a single bond; and R 5a , R 5b , R 5c , R 5d , R 5e , R 5f , R 5g  and R 5h  are each hydrogen. 
     
     
         56 . (canceled) 
     
     
         57 . (canceled) 
     
     
         58 . (canceled) 
     
     
         59 . (canceled) 
     
     
         60 . (canceled) 
     
     
         61 . (canceled) 
     
     
         62 . (canceled) 
     
     
         63 . (canceled) 
     
     
         64 . The compound of  claim 47 , wherein A 1  is an optionally substituted bicyclic C 3-10  cycloalkyl. 
     
     
         65 . (canceled) 
     
     
         66 . (canceled) 
     
     
         67 . (canceled) 
     
     
         68 . (canceled) 
     
     
         69 . The compound of  claim 47 , wherein A 1  is an optionally substituted phenyl. 
     
     
         70 . (canceled) 
     
     
         71 . The compound of  claim 47 , wherein A 1  is an optionally substituted monocyclic heteroaryl. 
     
     
         72 . (canceled) 
     
     
         73 . (canceled) 
     
     
         74 . (canceled) 
     
     
         75 . (canceled) 
     
     
         76 . (canceled) 
     
     
         77 . (canceled) 
     
     
         78 . (canceled) 
     
     
         79 . The compound of  claim 69 , wherein R 6  is an optionally substituted monocyclic heteroaryl. 
     
     
         80 . (canceled) 
     
     
         81 . (canceled) 
     
     
         82 . The compound of  claim 69 , wherein R 6  is an optionally substituted monocyclic heterocyclyl. 
     
     
         83 . (canceled) 
     
     
         84 . (canceled) 
     
     
         85 . (canceled) 
     
     
         86 . (canceled) 
     
     
         87 . (canceled) 
     
     
         88 . (canceled) 
     
     
         89 . A pharmaceutical composition comprising an effective amount of a compound of  claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent, excipient, or combination thereof. 
     
     
         90 . A method for ameliorating or treating a cancer comprising administering an effective amount of a compound of  claim 1 , or a pharmaceutically acceptable salt thereof, wherein the cancer is selected from the group consisting of a lung cancer, a pancreatic cancer, a colon cancer, a myeloid leukemia, a thyroid cancer, myelodysplastic syndrome (MDS), a bladder carcinoma, an epidermal carcinoma, a melanoma, a breast cancer, a prostate cancer, a head and neck cancer, an ovarian cancer, a brain cancer, a cancer of mesenchymal origin, a sarcoma, a tetracarcinoma, a neuroblastoma, a kidney carcinoma, a hepatoma, a non-Hodgkin's lymphoma, a multiple myeloma, an anaplastic thyroid carcinoma and neurofibromatosis. 
     
     
         91 . A method for inhibiting replication of a malignant growth or a tumor comprising contacting the growth or the tumor with an effective amount of a compound of  claim 1 , or a pharmaceutically acceptable salt thereof, wherein the malignant growth or tumor is due to a cancer is selected from the group consisting of a lung cancer, a pancreatic cancer, a colon cancer, a myeloid leukemia, a thyroid cancer, myelodysplastic syndrome (MDS), a bladder carcinoma, an epidermal carcinoma, a melanoma, a breast cancer, a prostate cancer, a head and neck cancer, an ovarian cancer, a brain cancer, a cancer of mesenchymal origin, a sarcoma, a tetracarcinoma, a neuroblastoma, a kidney carcinoma, a hepatoma, a non-Hodgkin's lymphoma, a multiple myeloma, an anaplastic thyroid carcinoma and neurofibromatosis. 
     
     
         92 . A method for ameliorating or treating a cancer comprising contacting a malignant growth or a tumor with an effective amount of a compound of  claim 1 , or a pharmaceutically acceptable salt thereof, wherein the malignant growth or tumor is due to a cancer is selected from the group consisting of a lung cancer, a pancreatic cancer, a colon cancer, a myeloid leukemia, a thyroid cancer, myelodysplastic syndrome (MDS), a bladder carcinoma, an epidermal carcinoma, a melanoma, a breast cancer, a prostate cancer, a head and neck cancer, an ovarian cancer, a brain cancer, a cancer of mesenchymal origin, a sarcoma, a tetracarcinoma, a neuroblastoma, a kidney carcinoma, a hepatoma, a non-Hodgkin's lymphoma, a multiple myeloma, an anaplastic thyroid carcinoma and neurofibromatosis. 
     
     
         93 . A method for inhibiting the activity of ERK1 and/or ERK2 comprising providing an effective amount of a compound of  claim 1 , or a pharmaceutically acceptable salt thereof, to a sample comprising a cancer cell, wherein the cancer cell is selected from the group consisting of a lung cancer cell, a pancreatic cancer cell, a colon cancer cell, a myeloid leukemia cell, a thyroid cancer cell, myelodysplastic syndrome (MDS) cell, a bladder carcinoma cell, an epidermal carcinoma cell, a melanoma cell, a breast cancer cell, a prostate cancer cell, a head and neck cancer cell, an ovarian cancer cell, a brain cancer cell, a cancer of mesenchymal origin cell, a sarcoma cell, a tetracarcinoma cell, a neuroblastoma cell, a kidney carcinoma cell, a hepatoma cell, a non-Hodgkin's lymphoma cell, a multiple myeloma cell and an anaplastic thyroid carcinoma cell and a neurofibromatosis cell. 
     
     
         94 . (canceled) 
     
     
         95 . (canceled) 
     
     
         96 . (canceled)

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