JP2022185012A - KRas G12Cの阻害剤及びそれを使用する方法 - Google Patents
KRas G12Cの阻害剤及びそれを使用する方法 Download PDFInfo
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- JP2022185012A JP2022185012A JP2022153381A JP2022153381A JP2022185012A JP 2022185012 A JP2022185012 A JP 2022185012A JP 2022153381 A JP2022153381 A JP 2022153381A JP 2022153381 A JP2022153381 A JP 2022153381A JP 2022185012 A JP2022185012 A JP 2022185012A
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- compound
- mmol
- pharmaceutically acceptable
- acceptable salt
- pyrimidin
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- 229960005294 triamcinolone Drugs 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- GUYPYYARYIIWJZ-CYEPYHPTSA-N triamcinolone benetonide Chemical compound O=C([C@]12[C@H](OC(C)(C)O1)C[C@@H]1[C@@]2(C[C@H](O)[C@]2(F)[C@@]3(C)C=CC(=O)C=C3CC[C@H]21)C)COC(=O)C(C)CNC(=O)C1=CC=CC=C1 GUYPYYARYIIWJZ-CYEPYHPTSA-N 0.000 description 1
- 229950006782 triamcinolone benetonide Drugs 0.000 description 1
- 229960004221 triamcinolone hexacetonide Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229930185603 trichostatin Natural products 0.000 description 1
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- HOGVTUZUJGHKPL-HTVVRFAVSA-N triciribine Chemical compound C=12C3=NC=NC=1N(C)N=C(N)C2=CN3[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O HOGVTUZUJGHKPL-HTVVRFAVSA-N 0.000 description 1
- 125000000165 tricyclic carbocycle group Chemical group 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- HDZZVAMISRMYHH-LITAXDCLSA-N tubercidin Chemical compound C1=CC=2C(N)=NC=NC=2N1[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O HDZZVAMISRMYHH-LITAXDCLSA-N 0.000 description 1
- 230000005751 tumor progression Effects 0.000 description 1
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- 108010012374 type IV collagen alpha3 chain Proteins 0.000 description 1
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- 229950008396 ulobetasol propionate Drugs 0.000 description 1
- BDSYKGHYMJNPAB-LICBFIPMSA-N ulobetasol propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]2(C)C[C@@H]1O BDSYKGHYMJNPAB-LICBFIPMSA-N 0.000 description 1
- 206010048828 underweight Diseases 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 229950005972 urelumab Drugs 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 201000000334 ureter transitional cell carcinoma Diseases 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 229950008737 vadimezan Drugs 0.000 description 1
- 206010046885 vaginal cancer Diseases 0.000 description 1
- 208000013139 vaginal neoplasm Diseases 0.000 description 1
- 229960002004 valdecoxib Drugs 0.000 description 1
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 229950010938 valspodar Drugs 0.000 description 1
- 108010082372 valspodar Proteins 0.000 description 1
- 108010060757 vasostatin Proteins 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- JNAHVYVRKWKWKQ-CYBMUJFWSA-N veliparib Chemical compound N=1C2=CC=CC(C(N)=O)=C2NC=1[C@@]1(C)CCCN1 JNAHVYVRKWKWKQ-CYBMUJFWSA-N 0.000 description 1
- 229960003895 verteporfin Drugs 0.000 description 1
- ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N verteporfin Chemical compound C=1C([C@@]2([C@H](C(=O)OC)C(=CC=C22)C(=O)OC)C)=NC2=CC(C(=C2C=C)C)=NC2=CC(C(=C2CCC(O)=O)C)=NC2=CC2=NC=1C(C)=C2CCC(=O)OC ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960000922 vinflunine Drugs 0.000 description 1
- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 229960000237 vorinostat Drugs 0.000 description 1
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 1
- 201000005102 vulva cancer Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 239000012130 whole-cell lysate Substances 0.000 description 1
- QDLHCMPXEPAAMD-QAIWCSMKSA-N wortmannin Chemical compound C1([C@]2(C)C3=C(C4=O)OC=C3C(=O)O[C@@H]2COC)=C4[C@@H]2CCC(=O)[C@@]2(C)C[C@H]1OC(C)=O QDLHCMPXEPAAMD-QAIWCSMKSA-N 0.000 description 1
- QDLHCMPXEPAAMD-UHFFFAOYSA-N wortmannin Natural products COCC1OC(=O)C2=COC(C3=O)=C2C1(C)C1=C3C2CCC(=O)C2(C)CC1OC(C)=O QDLHCMPXEPAAMD-UHFFFAOYSA-N 0.000 description 1
- 235000020138 yakult Nutrition 0.000 description 1
- 229940055760 yervoy Drugs 0.000 description 1
- 229950008250 zalutumumab Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
- 229950005752 zosuquidar Drugs 0.000 description 1
- CGTADGCBEXYWNE-JUKNQOCSSA-N zotarolimus Chemical compound N1([C@H]2CC[C@@H](C[C@@H](C)[C@H]3OC(=O)[C@@H]4CCCCN4C(=O)C(=O)[C@@]4(O)[C@H](C)CC[C@H](O4)C[C@@H](/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C3)OC)C[C@H]2OC)C=NN=N1 CGTADGCBEXYWNE-JUKNQOCSSA-N 0.000 description 1
- 229950009819 zotarolimus Drugs 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/07—Tetrapeptides
Abstract
Description
Aは、独立して、N又はCHであり;
Wは、独立して、N又はCHであり;
A及びWの一方又は両方は、Nであり;
R1及びR2は、独立して、分岐状又は直鎖状C1~6アルキルであり;
R3は、1つ又は2つのR5置換基によって置換されたフェニルであり;
R5は、独立して、1つ以上のハロ、-OH又はNH2から選択され;
R4は、ハロである)
の構造を有する化合物又はその立体異性体、その薬学的に許容される塩、その立体異性体の薬学的に許容される塩を含む。本発明の別の態様では、本発明の別の実施形態は、式(Ia)
Aは、独立して、N又はCHであり;
Wは、独立して、N又はCHであり;
A及びWの一方又は両方は、Nであり;
R1及びR2は、独立して、分岐状又は直鎖状C1~6アルキルであり;
R3は、1つ又は2つのR5置換基によって置換されたフェニルであり;
R5は、独立して、1つ以上のハロ、-OH又はNH2から選択され;及び
R4は、ハロである)
の構造を有する化合物又は又はその立体異性体、その薬学的に許容される塩、その立体異性体の薬学的に許容される塩を含む。
本明細書で提供されるのは、以下でより詳細に議論する、式I、Ia、II及びIIaの1つの構造を有するKRAS阻害剤である。
本明細書に開示される化合物は、いくつかの特定の方法を介して合成することができる。特定の合成経路及び下記の包括的スキームの概要を示す実施例は、溶媒、濃度、試薬、保護基、合成工程の順序、時間、温度などが十分に当業者の技術及び判断の範囲内で必要に応じて変更できることを容易に理解する、通常の能力を有する合成化学者に指針を提供することが意図されている。
また、本明細書では、例えば、希釈剤又は担体などの薬学的に許容される賦形剤と共に、本明細書に開示される化合物を含む医薬組成物も提供する。本発明での使用に好適な化合物及び医薬組成物としては、化合物がその意図された目的を達成するのに有効な量で投与できるものが挙げられる。化合物の投与は、以下により詳細に記載される。
本開示は、RAS媒介性細胞シグナル伝達を阻害する方法であって、細胞を、有効量の、本明細書に開示される1つ以上の化合物と接触させることを含む方法を提供する。RAS媒介性シグナル伝達の阻害は、当技術分野で知られる広範囲の種々の方法によって評価し、実証することができる。非限定的な例として、(a)RASのGTPase活性の減少;(b)GTP結合親和性の減少又はGDP結合親和性の増加;(c)GTPのKoffの増加又はGDPのKoffの減少;(d)pMEK、pERK又はpAKTレベルの減少など、RAS経路下流のシグナル伝達分子のレベルの減少;及び/又は(e)Rafを含むが、これに限定されない下流のシグナル伝達分子へのRAS複合体の結合の減少を示すことが挙げられる。上記の1つ以上を決定するために、キット及び市販のアッセイを利用することができる。
本開示は、他の経路若しくは同じ経路の他の成分を調節することが知られている薬剤又はさらに標的酵素の重複するセットが本開示の化合物又はその薬学的に許容される塩と組み合わせて使用される、併用療法の方法も提供する。一態様では、そのような治療は、相乗的又は相加的な治療効果を提供するために、本開示の1つ以上の化合物と、化学療法剤、治療抗体及び放射線治療との組み合わせを含むが、これらに限定されない。
4-((2S,5R,M)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-6-クロロ-7-(2-フルオロフェニル)-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R,M)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-6-クロロ-7-(2-フルオロ-6-ヒドロキシフェニル)-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R,M)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-7-(2-アミノ-6-フルオロフェニル)-6-クロロ-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R,M)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-6-フルオロ-7-(2-フルオロフェニル)-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R,M)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-6-フルオロ-7-(2-フルオロ-6-ヒドロキシフェニル)-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R,M)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-7-(2-アミノ-6-フルオロフェニル)-6-フルオロ-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-6-クロロ-1-(4,6-ジイソプロピルピリミジン-5-イル)-7-(2-フルオロフェニル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-6-クロロ-1-(4,6-ジイソプロピルピリミジン-5-イル)-7-(2-フルオロ-6-ヒドロキシフェニル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-7-(2-アミノ-6-フルオロフェニル)-6-クロロ-1-(4,6-ジイソプロピルピリミジン-5-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-1-(4,6-ジイソプロピルピリミジン-5-イル)-6-フルオロ-7-(2-フルオロフェニル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-1-(4,6-ジイソプロピルピリミジン-5-イル)-6-フルオロ-7-(2-フルオロ-6-ヒドロキシフェニル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-((2S,5R)-4-アクリロイル-2,5-ジメチルピペラジン-1-イル)-7-(2-アミノ-6-フルオロフェニル)-1-(4,6-ジイソプロピルピリミジン-5-イル)-6-フルオロピリド[2,3-d]ピリミジン-2(1H)-オン
(M)-4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-6-クロロ-7-(2-フルオロフェニル)-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
(M)-4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-6-クロロ-7-(2-フルオロ-6-ヒドロキシフェニル)-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
(M)-4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-7-(2-アミノ-6-フルオロフェニル)-6-クロロ-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
(M)-4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-6-フルオロ-7-(2-フルオロフェニル)-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
(M)-4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-6-フルオロ-7-(2-フルオロ-6-ヒドロキシフェニル)-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
(M)-4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-7-(2-アミノ-6-フルオロフェニル)-6-フルオロ-1-(2-イソプロピル-4-メチルピリジン-3-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-6-クロロ-1-(4,6-ジイソプロピルピリミジン-5-イル)-7-(2-フルオロフェニル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-6-クロロ-1-(4,6-ジイソプロピルピリミジン-5-イル)-7-(2-フルオロ-6-ヒドロキシフェニル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-7-(2-アミノ-6-フルオロフェニル)-6-クロロ-1-(4,6-ジイソプロピルピリミジン-5-イル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-1-(4,6-ジイソプロピルピリミジン-5-イル)-6-フルオロ-7-(2-フルオロフェニル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-1-(4,6-ジイソプロピルピリミジン-5-イル)-6-フルオロ-7-(2-フルオロ-6-ヒドロキシフェニル)ピリド[2,3-d]ピリミジン-2(1H)-オン
4-(4-アクリロイル-cis-3,5-ジメチルピペラジン-1-イル)-7-(2-アミノ-6-フルオロフェニル)-1-(4,6-ジイソプロピルピリミジン-5-イル)-6-フルオロピリド[2,3-d]ピリミジン-2(1H)-オン
表2における化合物に関して、以下のアッセイ条件を利用した:ヌクレオチド対交換アッセイ:G12C及びC118Aアミノ酸置換並びにN末端Hisタグの両方を含有する、精製GDP結合KRASタンパク質(aa 1-169)を、化合物用量反応滴定を用いてアッセイ緩衝液(25mM HEPES pH7.4、10mM MgCl2及び0.01%Triton X-100)中で5分間プレインキュベートした。化合物のプレインキュベーションに続いて、精製SOSタンパク質(aa 564-1049)及びGTP(Roche 10106399001)をアッセイウェルに加え、さらに30分間インキュベートした。SOS媒介性ヌクレオチド交換の阻害の程度を決定するために、精製GSTタグ付きcRAF(aa 1-149)、ニッケルキレートAlphaLISAアクセプタービーズ(PerkinElmer AL108R)及びAlphaScreenグルタチオンドナービーズ(PerkinElmer 6765302)をアッセイウェルに加え、5分間インキュベートした。次に、AlphaScreen(登録商標)技術を使用して、アッセイプレートをPerkinElmer EnVision Multilabel Readerで読み取り、4パラメータロジスティックモデルを使用してデータを分析し、IC50値を計算した。
Claims (81)
- Aは、Nである、請求項1に記載の化合物。
- Aは、CHである、請求項1に記載の化合物。
- Wは、Nである、請求項1に記載の化合物。
- Wは、CHである、請求項1に記載の化合物。
- R1は、CH3である、請求項1に記載の化合物。
- R1は、CH(CH3)2である、請求項1に記載の化合物。
- R2は、CH3である、請求項1に記載の化合物。
- R2は、CH(CH3)2である、請求項1に記載の化合物。
- R5は、ハロである、請求項1に記載の化合物。
- R5は、Fである、請求項11に記載の化合物。
- R5は、-OHである、請求項1に記載の化合物。
- R5は、-NH2である、請求項1に記載の化合物。
- R4は、ハロである、請求項1に記載の化合物。
- R4は、Clである、請求項19に記載の化合物。
- R4は、Fである、請求項19に記載の化合物。
- Aは、Nである、請求項22に記載の化合物。
- Aは、CHである、請求項22に記載の化合物。
- Wは、Nである、請求項22に記載の化合物。
- Wは、CHである、請求項22に記載の化合物。
- R1は、CH3である、請求項22に記載の化合物。
- R1は、CH(CH3)2である、請求項22に記載の化合物。
- R2は、CH3である、請求項22に記載の化合物。
- R2は、CH(CH3)2である、請求項22に記載の化合物。
- R5は、ハロである、請求項22に記載の化合物。
- R5は、Fである、請求項32に記載の化合物。
- R5は、-OHである、請求項22に記載の化合物。
- R5は、-NH2である、請求項22に記載の化合物。
- R4は、ハロである、請求項22に記載の化合物。
- R4は、Clである、請求項22に記載の化合物。
- R4は、Fである、請求項22に記載の化合物。
- 請求項1に記載の化合物及び薬学的に許容される賦形剤を含む医薬組成物。
- 請求項22に記載の化合物及び薬学的に許容される賦形剤を含む医薬組成物。
- 請求項43、44又は47~70のいずれか一項に記載の化合物及び薬学的に許容される賦形剤を含む医薬組成物。
- 細胞中のKRAS G12Cを阻害する方法であって、前記細胞を、請求項43、44又は47~70のいずれか一項に記載の化合物又は前記その薬学的に許容される塩と接触させることを含む方法。
- 対象におけるがんを治療する方法であって、治療有効量の、請求項1~44又は47~70のいずれか一項に記載の化合物又は前記その薬学的に許容される塩を前記対象に投与することを含む方法。
- 前記がんは、肺がん、膵臓がん又は大腸がんである、請求項73に記載の方法。
- 治療有効量の追加の薬学的に活性な化合物を前記対象に投与することをさらに含む、請求項1~44若しくは47~70のいずれか一項に記載の方法又はその薬学的に許容される塩。
- 前記追加の薬学的に活性な化合物は、カルフィルゾミブである、請求項75に記載の方法。
- 前記追加の薬学的に活性な化合物は、シタラビンである、請求項76に記載の方法。
- 対象においてがんを治療するための、請求項1~44若しくは47~70のいずれか一項に記載の化合物又は前記その薬学的に許容される塩の使用。
- 前記がんは、血液悪性腫瘍である、請求項78に記載の化合物。
- がんを治療するための薬剤の調製における、請求項1~44若しくは47~70のいずれか一項に記載の化合物又はその薬学的に許容される塩。
- 前記がんは、血液悪性腫瘍である、請求項80に記載の化合物。
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JP2024001117A (ja) | 2024-01-09 |
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US20220213101A1 (en) | 2022-07-07 |
MA50077A (fr) | 2020-07-15 |
SG11202001499WA (en) | 2020-03-30 |
CN111051306A (zh) | 2020-04-21 |
IL272512B (en) | 2022-07-01 |
US20200207766A1 (en) | 2020-07-02 |
WO2019051291A1 (en) | 2019-03-14 |
US11306087B2 (en) | 2022-04-19 |
JP7362868B2 (ja) | 2023-10-17 |
CA3075046A1 (en) | 2019-03-14 |
IL293443A (en) | 2022-07-01 |
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AU2018329920B2 (en) | 2022-12-01 |
UY37870A (es) | 2019-03-29 |
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