diff --git a/pkgs/development/python-modules/cachetools/default.nix b/pkgs/development/python-modules/cachetools/default.nix
index 39923013689a..3b70fce4ad53 100644
--- a/pkgs/development/python-modules/cachetools/default.nix
+++ b/pkgs/development/python-modules/cachetools/default.nix
@@ -2,23 +2,20 @@
   lib,
   buildPythonPackage,
   fetchFromGitHub,
-  pythonOlder,
   setuptools,
   pytestCheckHook,
 }:
 
 buildPythonPackage rec {
   pname = "cachetools";
-  version = "6.1.0";
+  version = "6.2.2";
   pyproject = true;
 
-  disabled = pythonOlder "3.7";
-
   src = fetchFromGitHub {
     owner = "tkem";
     repo = "cachetools";
     tag = "v${version}";
-    hash = "sha256-o3Ice6w7Ovot+nsmTpsl/toosZuVbi9RvRGs07W4H0Y=";
+    hash = "sha256-seoyqkrRQpRiMd5GTEvenjirn173Hq40Zuk1u7TvMPI=";
   };
 
   build-system = [ setuptools ];
diff --git a/pkgs/development/python-modules/pyproject-api/default.nix b/pkgs/development/python-modules/pyproject-api/default.nix
index 21232a08ca6e..ca0f18c286d9 100644
--- a/pkgs/development/python-modules/pyproject-api/default.nix
+++ b/pkgs/development/python-modules/pyproject-api/default.nix
@@ -20,23 +20,18 @@
   # tests
   pytest-mock,
   pytestCheckHook,
-  setuptools,
-  virtualenv,
-  wheel,
 }:
 
 buildPythonPackage rec {
   pname = "pyproject-api";
-  version = "1.9.1";
-  format = "pyproject";
-
-  disabled = pythonOlder "3.8";
+  version = "1.10.0";
+  pyproject = true;
 
   src = fetchFromGitHub {
     owner = "tox-dev";
     repo = "pyproject-api";
     tag = version;
-    hash = "sha256-Bf/FG5BNKbV3lfebEHFJ3cy80L1mWTYLXJfqPUzeNXc=";
+    hash = "sha256-fWlGGVjB43NPfBRFfOWqZUDQuqOdrFP7jsqq9xOfvaw=";
   };
 
   outputs = [
@@ -44,31 +39,23 @@ buildPythonPackage rec {
     "doc"
   ];
 
-  nativeBuildInputs = [
+  build-system = [
     hatchling
     hatch-vcs
+  ];
 
+  nativeBuildInputs = [
     # docs
     sphinxHook
     furo
     sphinx-autodoc-typehints
   ];
 
-  propagatedBuildInputs = [ packaging ] ++ lib.optionals (pythonOlder "3.11") [ tomli ];
+  dependencies = [ packaging ] ++ lib.optionals (pythonOlder "3.11") [ tomli ];
 
   nativeCheckInputs = [
     pytest-mock
     pytestCheckHook
-    setuptools
-    virtualenv
-    wheel
-  ];
-
-  disabledTests = [
-    # requires eol python2 interpreter
-    "test_can_build_on_python_2"
-    # different formatting for version specifier
-    "test_setuptools_prepare_metadata_for_build_wheel"
   ];
 
   pythonImportsCheck = [ "pyproject_api" ];
diff --git a/pkgs/development/python-modules/tox/default.nix b/pkgs/development/python-modules/tox/default.nix
index 93be8bfdb688..bb5b7fb092aa 100644
--- a/pkgs/development/python-modules/tox/default.nix
+++ b/pkgs/development/python-modules/tox/default.nix
@@ -5,10 +5,7 @@
   pythonOlder,
   packaging,
   pluggy,
-  py,
-  six,
   virtualenv,
-  toml,
   tomli,
   filelock,
   hatchling,
@@ -20,31 +17,27 @@
   cachetools,
   testers,
   tox,
+  typing-extensions,
 }:
 
 buildPythonPackage rec {
   pname = "tox";
-  version = "4.28.4";
-  format = "pyproject";
+  version = "4.32.0";
+  pyproject = true;
 
   src = fetchFromGitHub {
     owner = "tox-dev";
     repo = "tox";
     tag = version;
-    hash = "sha256-EKJsFf4LvfDi3OL6iNhKEBl5zlpdLET9RkfHEP7E9xU=";
+    hash = "sha256-n2tKjT0t8bm6iatukKKcGw0PC+5EJrQEABMIAumRaqE=";
   };
 
-  postPatch = ''
-    substituteInPlace pyproject.toml \
-      --replace "packaging>=22" "packaging"
-  '';
-
-  nativeBuildInputs = [
+  build-system = [
     hatchling
     hatch-vcs
   ];
 
-  propagatedBuildInputs = [
+  dependencies = [
     cachetools
     chardet
     colorama
@@ -52,13 +45,13 @@ buildPythonPackage rec {
     packaging
     platformdirs
     pluggy
-    py
     pyproject-api
-    six
-    toml
     virtualenv
   ]
-  ++ lib.optionals (pythonOlder "3.11") [ tomli ];
+  ++ lib.optionals (pythonOlder "3.11") [
+    tomli
+    typing-extensions
+  ];
 
   doCheck = false; # infinite recursion via devpi-client
 
diff --git a/pkgs/development/python-modules/virtualenv/default.nix b/pkgs/development/python-modules/virtualenv/default.nix
index 5d26d7d54820..24f2095011bf 100644
--- a/pkgs/development/python-modules/virtualenv/default.nix
+++ b/pkgs/development/python-modules/virtualenv/default.nix
@@ -3,75 +3,57 @@
   buildPythonPackage,
   pythonOlder,
   isPyPy,
-  cython,
   distlib,
-  fetchPypi,
+  fetchFromGitHub,
   filelock,
   flaky,
   hatch-vcs,
   hatchling,
-  importlib-metadata,
   platformdirs,
-  pytest-freezegun,
   pytest-mock,
-  pytest-timeout,
   pytestCheckHook,
   time-machine,
 }:
 
 buildPythonPackage rec {
   pname = "virtualenv";
-  version = "20.33.1";
-  format = "pyproject";
+  version = "20.35.4";
+  pyproject = true;
 
-  disabled = pythonOlder "3.7";
-
-  src = fetchPypi {
-    inherit pname version;
-    hash = "sha256-G0RHjZ4mGz+4uqXnSgyjvA4F8hqjYWe/nL+FDlQnZbg=";
+  src = fetchFromGitHub {
+    owner = "pypa";
+    repo = "virtualenv";
+    tag = version;
+    hash = "sha256-0PWIYU1/zXiOBUV/45rJsJwVlcqHeac68nRM2tvEPHo=";
   };
 
-  nativeBuildInputs = [
+  build-system = [
     hatch-vcs
     hatchling
   ];
 
-  propagatedBuildInputs = [
+  dependencies = [
     distlib
     filelock
     platformdirs
-  ]
-  ++ lib.optionals (pythonOlder "3.8") [ importlib-metadata ];
+  ];
 
   nativeCheckInputs = [
-    cython
     flaky
-    pytest-freezegun
     pytest-mock
-    pytest-timeout
     pytestCheckHook
   ]
   ++ lib.optionals (!isPyPy) [ time-machine ];
 
-  preCheck = ''
-    export HOME=$(mktemp -d)
-  '';
-
   disabledTestPaths = [
     # Ignore tests which require network access
     "tests/unit/create/test_creator.py"
-    "tests/unit/seed/embed/test_bootstrap_link_via_app_data.py"
+    "tests/unit/create/via_global_ref/test_build_c_ext.py"
   ];
 
   disabledTests = [
     # Network access
-    "test_create_no_seed"
     "test_seed_link_via_app_data"
-    # Permission Error
-    "test_bad_exe_py_info_no_raise"
-    # https://github.com/pypa/virtualenv/issues/2933
-    # https://github.com/pypa/virtualenv/issues/2939
-    "test_py_info_cache_invalidation_on_py_info_change"
   ]
   ++ lib.optionals (pythonOlder "3.11") [ "test_help" ]
   ++ lib.optionals isPyPy [