create table tmp123 ( user_id number, cmd_time number, login_name varchar2(100), login_time date );

truncate table tmp123;

insert into tmp123 values ( 1, 10, 'user1_login1', to_date( '01.10.2019','dd.mm.yyyy') );
insert into tmp123 values ( 1, 10, 'user1_login2', to_date( '02.10.2019','dd.mm.yyyy') );
insert into tmp123 values ( 2, 5, 'user2_login1', to_date( '01.10.2019','dd.mm.yyyy') );
insert into tmp123 values ( 3, 2, 'user3_login1', to_date( '01.10.2019','dd.mm.yyyy') );
insert into tmp123 values ( 3, 4, 'user3_login2', to_date( '02.10.2019','dd.mm.yyyy') );
insert into tmp123 values ( 3, 2, 'user3_login3', to_date( '03.10.2019','dd.mm.yyyy') );

select 
  user_id,
  sum_cmd_time,
  login_name as last_login_name,
  login_time as last_login_time
from (
  select 
    user_id,
    sum(cmd_time) over (partition by user_id) as sum_cmd_time,
    row_number() over (partition by user_id order by login_time desc) as login_rownum,
    login_name,
    login_time
  from tmp123
)
where login_rownum=1
order by sum_cmd_time desc;