diff --git a/sqlalchemy-stubs/sql/operators.pyi b/sqlalchemy-stubs/sql/operators.pyi
index 89a08e1..37d5ac1 100644
--- a/sqlalchemy-stubs/sql/operators.pyi
+++ b/sqlalchemy-stubs/sql/operators.pyi
@@ -31,6 +31,7 @@ class ColumnOperators(Operators):
     def __eq__(self, other): ...
     def __ne__(self, other): ...
     def is_distinct_from(self, other): ...
+    def is_not_distinct_from(self, other): ...
     def isnot_distinct_from(self, other): ...
     def __gt__(self, other): ...
     def __ge__(self, other): ...
@@ -43,10 +44,14 @@ class ColumnOperators(Operators):
     def like(self, other: Text, escape: Optional[Any] = ...): ...
     def ilike(self, other: Text, escape: Optional[Any] = ...): ...
     def in_(self, other: Union[Iterable[Any], BindParameter, Select, Alias]): ...
+    def not_in(self, other: Union[Iterable[Any], BindParameter, Select, Alias]): ...
     def notin_(self, other: Union[Iterable[Any], BindParameter, Select, Alias]): ...
+    def not_like(self, other, escape: Optional[Any] = ...): ...
     def notlike(self, other, escape: Optional[Any] = ...): ...
+    def not_ilike(self, other, escape: Optional[Any] = ...): ...
     def notilike(self, other, escape: Optional[Any] = ...): ...
     def is_(self, other): ...
+    def is_not(self, other): ...
     def isnot(self, other): ...
     def startswith(self, other: str, **kwargs): ...
     def endswith(self, other, **kwargs): ...
@@ -54,7 +59,9 @@ class ColumnOperators(Operators):
     def match(self, other, **kwargs): ...
     def desc(self) -> UnaryExpression: ...
     def asc(self) -> UnaryExpression: ...
+    def nulls_first(self): ...
     def nullsfirst(self): ...
+    def nulls_last(self): ...
     def nullslast(self): ...
     def collate(self, collation): ...
     def __radd__(self, other): ...
@@ -77,11 +84,15 @@ class ColumnOperators(Operators):
 def from_(): ...
 def as_(): ...
 def exists(): ...
+def is_true(a): ...
 def istrue(a): ...
+def is_false(a): ...
 def isfalse(a): ...
 def is_distinct_from(a, b): ...
+def is_not_distinct_from(a, b): ...
 def isnot_distinct_from(a, b): ...
 def is_(a, b): ...
+def is_not(a, b): ...
 def isnot(a, b): ...
 def collate(a, b): ...
 def op(a, opstring, b): ...
@@ -90,25 +101,33 @@ def notlike_op(a, b, escape: Optional[Any] = ...): ...
 def ilike_op(a, b, escape: Optional[Any] = ...): ...
 def notilike_op(a, b, escape: Optional[Any] = ...): ...
 def between_op(a, b, c, symmetric: bool = ...): ...
+def not_between_op(a, b, c, symmetric: bool = ...): ...
 def notbetween_op(a, b, c, symmetric: bool = ...): ...
 def in_op(a, b): ...
+def not_in_op(a, b): ...
 def notin_op(a, b): ...
 def distinct_op(a): ...
 def any_op(a): ...
 def all_op(a): ...
 def startswith_op(a, b, escape: Optional[Any] = ...): ...
+def not_startswith_op(a, b, escape: Optional[Any] = ...): ...
 def notstartswith_op(a, b, escape: Optional[Any] = ...): ...
 def endswith_op(a, b, escape: Optional[Any] = ...): ...
+def not_endswith_op(a, b, escape: Optional[Any] = ...): ...
 def notendswith_op(a, b, escape: Optional[Any] = ...): ...
 def contains_op(a, b, escape: Optional[Any] = ...): ...
+def not_contains_op(a, b, escape: Optional[Any] = ...): ...
 def notcontains_op(a, b, escape: Optional[Any] = ...): ...
 def match_op(a, b, **kw): ...
+def not_match_op(a, b, **kw): ...
 def notmatch_op(a, b, **kw): ...
 def comma_op(a, b): ...
 def concat_op(a, b): ...
 def desc_op(a): ...
 def asc_op(a): ...
+def nulls_first_op(a): ...
 def nullsfirst_op(a): ...
+def nulls_last_op(a): ...
 def nullslast_op(a): ...
 def json_getitem_op(a, b): ...
 def json_path_getitem_op(a, b): ...