https://qiita.com/aiwister/items/f4f84c973a527e6afea9#comment-d869c63cff04566ad99f

make_number.py

from itertools import permutations

def exp(a, b, *c):
    if c:
        for op in '+-*/':
            yield from exp(f'({a}{op}{b})', *c)
            yield from exp(f'({b}{op}{a})', *c)
            for i in range(1, len(c) + 1):
                yield from exp(*c[:i], f'({a}{op}{b})', *c[i:])
                yield from exp(*c[:i], f'({b}{op}{a})', *c[i:])
    else:
        for op in '+-*/':
            yield f'({a}{op}{b})'
            yield f'({b}{op}{a})'

def make(numbers, target):
    for e in set(e for n in permutations(numbers) for e in exp(*n)):
        try:
            if eval(e) == target:
                yield e
        except ZeroDivisionError:
            pass

def main():
    print(list(make([1, 1, 9, 9], 10)))

if __name__ == "__main__":
    main()