From daa6e78e4b810eff826f995aa52f9e38197f1b7e Mon Sep 17 00:00:00 2001
From: Jo <46752250+georgesittas@users.noreply.github.com>
Date: Mon, 14 Oct 2024 18:24:44 +0300
Subject: [PATCH] Fix(optimizer): handle subquery predicate substitution
 correctly in de morgan's rule (#4240)

---
 sqlglot/optimizer/simplify.py         | 14 +++++++++++---
 tests/fixtures/optimizer/simplify.sql |  3 +++
 2 files changed, 14 insertions(+), 3 deletions(-)

diff --git a/sqlglot/optimizer/simplify.py b/sqlglot/optimizer/simplify.py
index bafc86238..68a4a1501 100644
--- a/sqlglot/optimizer/simplify.py
+++ b/sqlglot/optimizer/simplify.py
@@ -206,6 +206,11 @@ def rewrite_between(expression: exp.Expression) -> exp.Expression:
     exp.NEQ: exp.EQ,
 }
 
+COMPLEMENT_SUBQUERY_PREDICATES = {
+    exp.All: exp.Any,
+    exp.Any: exp.All,
+}
+
 
 def simplify_not(expression):
     """
@@ -218,9 +223,12 @@ def simplify_not(expression):
         if is_null(this):
             return exp.null()
         if this.__class__ in COMPLEMENT_COMPARISONS:
-            return COMPLEMENT_COMPARISONS[this.__class__](
-                this=this.this, expression=this.expression
-            )
+            right = this.expression
+            complement_subquery_predicate = COMPLEMENT_SUBQUERY_PREDICATES.get(right.__class__)
+            if complement_subquery_predicate:
+                right = complement_subquery_predicate(this=right.this)
+
+            return COMPLEMENT_COMPARISONS[this.__class__](this=this.this, expression=right)
         if isinstance(this, exp.Paren):
             condition = this.unnest()
             if isinstance(condition, exp.And):
diff --git a/tests/fixtures/optimizer/simplify.sql b/tests/fixtures/optimizer/simplify.sql
index fa2dc7964..1842e5550 100644
--- a/tests/fixtures/optimizer/simplify.sql
+++ b/tests/fixtures/optimizer/simplify.sql
@@ -140,6 +140,9 @@ TRUE;
 COALESCE(x, y) <> ALL (SELECT z FROM w);
 COALESCE(x, y) <> ALL (SELECT z FROM w);
 
+SELECT NOT (2 <> ALL (SELECT 2 UNION ALL SELECT 3));
+SELECT 2 = ANY(SELECT 2 UNION ALL SELECT 3);
+
 --------------------------------------
 -- Absorption
 --------------------------------------