JP2021523099A - Kras g12c阻害剤及び同一物の使用方法 - Google Patents
Kras g12c阻害剤及び同一物の使用方法 Download PDFInfo
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- JP2021523099A JP2021523099A JP2020560752A JP2020560752A JP2021523099A JP 2021523099 A JP2021523099 A JP 2021523099A JP 2020560752 A JP2020560752 A JP 2020560752A JP 2020560752 A JP2020560752 A JP 2020560752A JP 2021523099 A JP2021523099 A JP 2021523099A
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- alkyl
- alkylene
- heterocycloalkyl
- compound according
- cycloalkyl
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- LIRYPHYGHXZJBZ-UHFFFAOYSA-N trametinib Chemical compound CC(=O)NC1=CC=CC(N2C(N(C3CC3)C(=O)C3=C(NC=4C(=CC(I)=CC=4)F)N(C)C(=O)C(C)=C32)=O)=C1 LIRYPHYGHXZJBZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 206010044412 transitional cell carcinoma Diseases 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 108010075758 trebananib Proteins 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
- 229950001353 tretamine Drugs 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 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
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
- 229960001099 trimetrexate Drugs 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000005751 tumor progression Effects 0.000 description 1
- 229940094060 tykerb Drugs 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 229950009811 ubenimex Drugs 0.000 description 1
- 229960001055 uracil mustard Drugs 0.000 description 1
- 229950005972 urelumab Drugs 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 208000037965 uterine sarcoma Diseases 0.000 description 1
- 238000001291 vacuum drying Methods 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
- 229960000653 valrubicin Drugs 0.000 description 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229950011257 veliparib Drugs 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
- JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-CFWMRBGOSA-N 0.000 description 1
- 229960003048 vinblastine Drugs 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
- 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
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 1
- 229960000237 vorinostat Drugs 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
- 235000020138 yakult Nutrition 0.000 description 1
- 229940055760 yervoy 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
- 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
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 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
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- C07K16/28—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
- C07K16/30—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants from tumour cells
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Abstract
Description
E1及びE2は、それぞれ独立して、N若しくはCR1であり;
Rpは、独立して、H、ヒドロキシ、−C1〜6アルキル、ハロ、−C1〜4ハロアルキル、−C1〜4アルコキシ、−NH−C1〜4アルキル、−N(C1〜4アルキル)2、シアノ、−C2〜3アルケニル、−C2〜3アルキニル、−C3〜14シクロアルキル、−C2〜14ヘテロシクロアルキル、アリール若しくはヘテロアリールであり;
R1は、独立して、H、ヒドロキシ、−C1〜6アルキル、−C1〜6ハロアルキル、−C1〜6アルコキシ、−NH−C1〜6アルキル、−N(C1〜4アルキル)2、シアノ若しくはハロであり;
R2は、ハロ、−C1〜6アルキル、−C1〜6ハロアルキル、−OR2a、−N(R2a)2、−C2〜6アルケニル、−C2〜6アルキニル、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、アリール、ヘテロアリール、−C0〜3アルキレン−C6〜14アリール若しくは−C0〜3アルキレン−C2〜14ヘテロアリールであり、各R2aは、独立して、H、−C1〜6アルキル、−C1〜6ハロアルキル、−C3〜14シクロアルキル、−C2〜14ヘテロシクロアルキル、−C2〜6アルケニル、−C2〜6アルキニル、アリール若しくはヘテロアリールであり、又は2つのR2a置換基は、それらが結合している窒素原子と共に3〜7員環を形成し;
R3は、ハロ、−C1〜6アルキル、−C1〜6ハロアルキル、−C1〜6アルコキシ、C3〜6シクロアルキル、−C2〜14ヘテロシクロアルキル、−C2〜6アルケニル、−C2〜6アルキニル、アリール若しくはヘテロアリールであり;
R4は、
環Aは、単環式の4〜7員環、又は二環式の、架橋した、縮合した、若しくはスピロの6〜11員環であり;
Lは、結合、−C1〜6アルキレン、−O−C0〜6アルキレン、−S−C0〜6アルキレン若しくは−NH−C0〜6アルキレンであり、−C2〜6アルキレン、−O−C2〜6アルキレン、−S−C2〜6アルキレン及びNH−C2〜6アルキレンについては、アルキレン基の1個の炭素原子は、任意選択的にO、S若しくはNHで置換することができ;
R4aは、H、−C1〜6アルキル、C2〜6アルキニル、C1〜6アルキレン−O−C1〜4アルキル、C1〜6アルキレン−OH、C1〜6ハロアルキル、シクロアルキル、ヘテロシクロアルキル、C0〜3アルキレン−C3〜14シクロアルキル、C0〜3アルキレン−C2〜14ヘテロシクロアルキル、アリール、ヘテロアリール、C0〜3アルキレン−C6〜14アリールであり、又は
R5及びR6は、それぞれ独立して、H、ハロ、−C1〜6アルキル、−C2〜6アルキニル、−C1〜6アルキレン−O−C1〜4アルキル、−C1〜6アルキレン−OH、−C1〜6ハロアルキル、−C1〜6アルキレンアミン、−C0〜6アルキレン−アミド、−C0〜3アルキレン−C(O)OH、−C0〜3アルキレン−C(O)OC1〜4アルキル、−C1〜6アルキレン−O−アリール、−C0〜3アルキレン−C(O)C1〜4アルキレン−OH、シクロアルキル、ヘテロシクロアルキル、アリール、ヘテロアリール、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−C0〜3アルキレン−C6〜14アリール、−C0〜3アルキレン−C2〜14ヘテロアリール若しくはシアノであり、又はR5及びR6は、それらが結合している原子と共に4〜6員環を形成し;
R7は、H若しくはC1〜6アルキルであり、又はR7及びR5は、それらが結合している原子と共に4〜6員環を形成し;
R8は、−C1〜6アルキル、−C0〜3アルキレン−C6〜14アリール、−C0〜3アルキレン−C3〜14ヘテロアリール、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−C1〜6アルコキシ、−O−C0〜3アルキレン−C6〜14アリール、−O−C0〜3アルキレン−C3〜14ヘテロアリール、−O−C0〜3アルキレン−C3〜14シクロアルキル、−O−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−NH−C1〜8アルキル、−N(C1〜8アルキル)2、−NH−C0〜3アルキレン−C6〜14アリール、−NH−C0〜3アルキレン−C2〜14ヘテロアリール、−NH−C0〜3アルキレン−C3〜14シクロアルキル、−NH−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、ハロ、シアノ若しくはC1〜6アルキレン−アミンであり;
ここでRp、R2、R2a、R3、R4、R4a、R5、R6、R7及びR8置換基の何れかのヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、シクロアルキル、スピロシクロアルキル、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、C=O基を含むことができ、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含み得る;
ここでRp、R1、R2、R2a、R3、R4、R4a、L、R5、R6、R7及びR8置換基の何れかの−C1〜6アルキル、−C2〜6アルケニル、−C2〜6アルキニル及び−OC1〜6アルキルは、非置換であるか、又はOH、−OC1〜6アルキル、−C1〜6アルキル−O−C1〜6アルキル、ハロ、−O−ハロC1〜6アルキル、−CN、−NRaRb、−(NRaRbRc)n、−OSO2Ra、−SO2Ra、−(CH2CH2O)nCH3、−(=O)、−C(=O)、−C(=O)Ra、−OC(=O)Ra、−C(=O)ORa、−C(=O)NRaRb、−O−SiRaRbRc、−SiRaRbRc、−O−(3〜10員のヘテロシクロアルキル)、6〜12員のアリール若しくはヘテロアリール、5〜12員のスピロシクロアルキル若しくはスピロヘテロシクロアルキル、3〜12員のシクロアルケニル、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基から独立して選択される1、2若しくは3つのR9置換基によって置換されており、ヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、シクロアルキル、スピロシクロアルキル、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、C=O基を含むことができ、更にスピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含むことができ;
ここでRp、R1、R2、R2a、R3、R4、R4a、R5、R6、R7、R8及びR9置換基の何れかのアリール、ヘテロアリール、シクロアルキル及びヘテロシクロアルキル基は、非置換であるか、又はOH、ハロ、−NRcRd、−C1〜6アルキル、−OC1〜6アルキル、−C1〜6アルキル−OH、−C1〜6アルキル−O−C1〜6アルキル、C1〜6ハロアルキル、−O−ハロC1〜6アルキル、−SO2Rc、−CN、−C(=O)NRcRd、−C(=O)Rc、−OC(=O)Ra、−C(=O)ORc、6〜12員のアリール若しくはヘテロアリール、5〜12員のスピロシクロアルキル若しくはスピロヘテロシクロアルキル、3〜12員のシクロアルケニル、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基から独立して選択される1、2、3若しくは4つのR10置換基で置換されてよく、R10のヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、R10のシクロアルキル、スピロシクロアルキル及びスピロヘテロシクロアルキル基又はR10のヘテロシクロアルキル基はC=O基を含むことができ、更にスピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含むことができ;
ここで各Ra、Rb、Rc及びRdは、独立して水素、OH、−C1〜6アルキル、−(CH2CH2O)nCH3、−NR11R11、−C1〜6アルキル−NR11R11、フェニル、−C1〜6アルキル−C(=O)OH、−C1〜6アルキル−C(=O)−O−C1〜6アルキル、−C1〜6アルキル−3〜12員のシクロアルキル、−C1〜6アルキル−3〜12員のヘテロシクロアルキル、−C1〜6アルキル−6〜12員のヘテロアリール、6〜12員のアリール若しくはヘテロアリール、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基であり、Ra、Rb、Rc及びRdのヘテロアリール基、ヘテロシクロアルキル基、又はRa、Rb、Rc及びRdのC1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、Ra、Rb、Rc及びRdのシクロアルキル及びヘテロシクロアルキル基並びにRa、Rb、Rc及びRdの−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、二重結合を含むことができ、更にRa、Rb、Rc及びRdのシクロアルキル及びヘテロシクロアルキル基並びにRa、Rb、Rc及びRdの−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、C=O基を含有することができ;及び
Ra、Rb、Rc及びRdのアルキル、アリール、ヘテロアリール、シクロアルキル、ヘテロシクロアルキル基又はRa、Rb、Rc及びRdの−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、非置換であるか、又は1、2、3若しくは4つのR12置換基で置換することができ、ここで各R12は、H、OH、ハロ、−C1〜6アルキル、N(CH3)2、−C1〜6ハロアルキル、C(=O)CH3、−C(=O)OCH3若しくは−C1〜6アルキル−O−C1〜6アルキルから独立して選択される]の構造を有する化合物;又は
その立体異性体、そのアトロプ異性体、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若しくはそのアトロプ異性体の薬学的に許容される塩を提供する。
その立体異性体、そのアトロプ異性体、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若しくはそのアトロプ異性体の薬学的に許容される塩をもたらす。
略語:本明細書では、下記の略語を使用することができる。
本明細書で開示した化合物は、本明細書で開示した化合物の1個以上の原子が、同じ原子番号を有するが、通常、天然に見出される原子質量又は質量数と異なる原子質量又は質量数を有する原子によって置換された、全ての薬学的に許容される同位体標識化合物を含む。開示した化合物に組み込むことができる同位体の例としては、水素、炭素、窒素、酸素、リン、フッ素、塩素及びヨウ素の同位体、例えば、それぞれ2H、3H、11C、13C、14C、13N、15N、15O、17O、18O、31P、32P、35S、18F、36Cl、123I及び125Iが挙げられる。これらの放射性標識化合物は、例えば、作用部位若しくは作用様式、又は薬理学的に重要な作用部位に対する結合親和性を同定することによって、化合物の有効性の決定若しくは測定を助けるのに有用であろう。本開示の特定の同位体標識化合物、例えば、放射性同位体を組み込んだものは、薬剤及び/又は基質組織分布の研究において有用である。放射性同位体のトリチウム、即ち3H、及び炭素14、即ち14Cは、取り込みの容易さ及び検知の容易な手段の観点から、この目的ために特に有効である。
Rpは、独立して、H、ヒドロキシ、−C1〜6アルキル、ハロ、−C1〜4ハロアルキル、−C1〜4アルコキシ、−NH−C1〜4アルキル、−N(C1〜4アルキル)2、シアノ、−C2〜3アルケニル、−C2〜3アルキニル、−C3〜14シクロアルキル、−C2〜14ヘテロシクロアルキル、アリール若しくはヘテロアリールであり;
R1は、独立して、H、ヒドロキシ、−C1〜6アルキル、−C1〜6ハロアルキル、−C1〜6アルコキシ、−NH−C1〜6アルキル、−N(C1〜4アルキル)2、シアノ若しくはハロであり;
R2は、ハロ、−C1〜6アルキル、−C1〜6ハロアルキル、−OR2a、−N(R2a)2、−C2〜6アルケニル、−C2〜6アルキニル、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、アリール、ヘテロアリール、−C0〜3アルキレン−C6〜14アリール若しくは−C0〜3アルキレン−C2〜14ヘテロアリールであり、各R2aは、独立して、H、−C1〜6アルキル、−C1〜6ハロアルキル、−C3〜14シクロアルキル、−C2〜14ヘテロシクロアルキル、−C2〜6アルケニル、−C2〜6アルキニル、アリール若しくはヘテロアリールであり、又は2つの2a置換基は、それらが結合している窒素原子と共に3〜7員環を形成し;
R3は、ハロ、−C1〜6アルキル、−C1〜6ハロアルキル、−C1〜6アルコキシ、C3〜6シクロアルキル、−C2〜14ヘテロシクロアルキル、−C2〜6アルケニル、−C2〜6アルキニル、アリール若しくはヘテロアリールであり;
R4は、
環Aは、単環式の4〜7員環、又は二環式の、架橋した、縮合した、若しくはスピロの6〜11員環であり;
Lは、結合、−C1〜6アルキレン、−O−C0〜6アルキレン、−S−C0〜6アルキレン若しくは−NH−C0〜6アルキレンであり、−C2〜6アルキレン、−O−C2〜6アルキレン、−S−C2〜6アルキレン及びNH−C2〜6アルキレンについては、アルキレン基の1個の炭素原子は、任意選択的にO、S若しくはNHで置換することができ;
R4aは、H、−C1〜6アルキル、C2〜6アルキニル、C1〜6アルキレン−O−C1〜4アルキル、C1〜6アルキレン−OH、C1〜6ハロアルキル、シクロアルキル、ヘテロシクロアルキル、C0〜3アルキレン−C3〜14シクロアルキル、C0〜3アルキレン−C2〜14ヘテロシクロアルキル、アリール、ヘテロアリール、C0〜3アルキレン−C6〜14アリールであり、又は
R5及びR6は、それぞれ独立して、H、ハロ、−C1〜6アルキル、−C2〜6アルキニル、−C1〜6アルキレン−O−C1〜4アルキル、−C1〜6アルキレン−OH、−C1〜6ハロアルキル、−C1〜6アルキレンアミン、−C0〜6アルキレン−アミド、−C0〜3アルキレン−C(O)OH、−C0〜3アルキレン−C(O)OC1〜4アルキル、−C1〜6アルキレン−O−アリール、−C0〜3アルキレン−C(O)C1〜4アルキレン−OH、シクロアルキル、ヘテロシクロアルキル、アリール、ヘテロアリール、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−C0〜3アルキレン−C6〜14アリール、−C0〜3アルキレン−C2〜14ヘテロアリール若しくはシアノであり、又はR5及びR6は、それらが結合している原子と共に4〜6員環を形成し;
R7は、H若しくはC1〜6アルキルであり、又はR7及びR5は、それらが結合している原子と共に4〜6員環を形成し;
R8は、−C1〜6アルキル、−C0〜3アルキレン−C6〜14アリール、−C0〜3アルキレン−C3〜14ヘテロアリール、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−C1〜6アルコキシ、−O−C0〜3アルキレン−C6〜14アリール、−O−C0〜3アルキレン−C3〜14ヘテロアリール、−O−C0〜3アルキレン−C3〜14シクロアルキル、−O−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−NH−C1〜8アルキル、−N(C1〜8アルキル)2、−NH−C0〜3アルキレン−C6〜14アリール、−NH−C0〜3アルキレン−C2〜14ヘテロアリール、−NH−C0〜3アルキレン−C3〜14シクロアルキル、−NH−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、ハロ、シアノ若しくはC1〜6アルキレン−アミンであり;
ここでRp、R2、R2a、R3、R4、R4a、R5、R6、R7及びR8置換基の何れかのヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、シクロアルキル、スピロシクロアルキル、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、C=O基を含むことができ、更にスピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含み得る;
ここでRp、R1、R2、R2a、R3、R4、R4a、L、R5、R6、R7及びR8置換基の何れかの−C1〜6アルキル、−C2〜6アルケニル、−C2〜6アルキニル及び−OC1〜6アルキルの何れかは、非置換であるか、又はOH、−OC1〜6アルキル、−C1〜6アルキル−O−C1〜6アルキル、ハロ、−O−ハロC1〜6アルキル、−CN、−NRaRb、−(NRaRbRc)n、−OSO2Ra、−SO2Ra、−(CH2CH2O)nCH3、−(=O)、−C(=O)、−C(=O)Ra、−OC(=O)Ra、−C(=O)ORa、−C(=O)NRaRb、−O−SiRaRbRc、−SiRaRbRc、−O−(3〜10員のヘテロシクロアルキル)、6〜12員のアリール若しくはヘテロアリール、5〜12員のスピロシクロアルキル若しくはスピロヘテロシクロアルキル、3〜12員のシクロアルケニル、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基から独立して選択される1、2若しくは3つのR9置換基によって置換されており、ヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、シクロアルキル、スピロシクロアルキル、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、C=O基を含むことができ、更にスピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含むことができ;
ここでRp、R1、R2、R2a、R3、R4、R4a、R5、R6、R7、R8及びR9置換基の何れかのアリール、ヘテロアリール、シクロアルキル及びヘテロシクロアルキル基は、非置換であるか、又はOH、ハロ、−NRcRd、−C1〜6アルキル、−OC1〜6アルキル、−C1〜6アルキル−OH、−C1〜6アルキル−O−C1〜6アルキル、C1〜6ハロアルキル、−O−ハロC1〜6アルキル、−SO2Rc、−CN、−C(=O)NRcRd、−C(=O)Rc、−OC(=O)Ra、−C(=O)ORc、6〜12員のアリール若しくはヘテロアリール、5〜12員のスピロシクロアルキル若しくはスピロヘテロシクロアルキル、3〜12員のシクロアルケニル、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基から独立して選択される1、2、3若しくは4つのR10置換基で置換されてよく、R10のヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、R10のシクロアルキル、スピロシクロアルキル及びスピロヘテロシクロアルキル基又はR10のヘテロシクロアルキル基はC=O基を含むことができ、更にスピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含むことができ;
ここで各Ra、Rb、Rc及びRdは、独立して水素、OH、−C1〜6アルキル、−(CH2CH2O)nCH3、−NR11R11、−C1〜6アルキル−NR11R11、フェニル、−C1〜6アルキル−C(=O)OH、−C1〜6アルキル−C(=O)−O−C1〜6アルキル、−C1〜6アルキル−3〜12員のシクロアルキル、−C1〜6アルキル−3〜12員のヘテロシクロアルキル、−C1〜6アルキル−6〜12員のヘテロアリール、6〜12員のアリール若しくはヘテロアリール、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基であり、Ra、Rb、Rc及びRdのヘテロアリール基、ヘテロシクロアルキル基、又はRa、Rb、Rc及びRdのC1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、Ra、Rb、Rc及びRdのシクロアルキル及びヘテロシクロアルキル基並びにRa、Rb、Rc及びRdの−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、二重結合を含むことができ、更にRa、Rb、Rc及びRdのシクロアルキル及びヘテロシクロアルキル基並びにRa、Rb、Rc及びRdの−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、C=O基を含有することができ;及び
Ra、Rb、Rc及びRdのアルキル、アリール、ヘテロアリール、シクロアルキル、ヘテロシクロアルキル基又はRa、Rb、Rc及びRdの−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、非置換であるか、又は1、2、3若しくは4つのR12置換基で置換することができ、ここで各R12は、H、OH、ハロ、−C1〜6アルキル、N(CH3)2、−C1〜6ハロアルキル、C(=O)CH3、−C(=O)OCH3若しくは−C1〜6アルキル−O−C1〜6アルキルから独立して選択される]の構造を有する化合物;
その立体異性体、そのアトロプ異性体、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若しくはそのアトロプ異性体の薬学的に許容される塩を提供する。
実施形態1
第一実施形態では、本発明は、式(I):
E1及びE2は、それぞれ独立して、N若しくはCR1であり;
Rpは、独立して、H、ヒドロキシ、−C1〜6アルキル、ハロ、−C1〜4ハロアルキル、−C1〜4アルコキシ、−NH−C1〜4アルキル、−N(C1〜4アルキル)2、シアノ、−C2〜3アルケニル、−C2〜3アルキニル、−C3〜14シクロアルキル、−C2〜14ヘテロシクロアルキル、アリール若しくはヘテロアリールであり;
R1は、独立して、H、ヒドロキシ、−C1〜6アルキル、−C1〜6ハロアルキル、−C1〜6アルコキシ、−NH−C1〜6アルキル、−N(C1〜4アルキル)2、シアノ若しくはハロであり;
R2は、ハロ、−C1〜6アルキル、−C1〜6ハロアルキル、−OR2a、−N(R2a)2、−C2〜6アルケニル、−C2〜6アルキニル、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、アリール、ヘテロアリール、−C0〜3アルキレン−C6〜14アリール若しくは−C0〜3アルキレン−C2〜14ヘテロアリールであり、及び各R2aは、独立して、H、−C1〜6アルキル、−C1〜6ハロアルキル、−C3〜14シクロアルキル、−C2〜14ヘテロシクロアルキル、−C2〜6アルケニル、−C2〜6アルキニル、アリール若しくはヘテロアリールであり、又は2つの2a置換基は、それらが結合している窒素原子と共に3〜7員環を形成し;
R3は、ハロ、−C1〜6アルキル、−C1〜6ハロアルキル、−C1〜6アルコキシ、C3〜6シクロアルキル、−C2〜14ヘテロシクロアルキル、−C2〜6アルケニル、−C2〜6アルキニル、アリール若しくはヘテロアリールであり;
R4は、
環Aは、単環式の4〜7員環、又は二環式の、架橋した、縮合した、若しくはスピロの6〜11員環であり;
Lは、結合、−C1〜6アルキレン、−O−C0〜6アルキレン、−S−C0〜6アルキレン若しくは−NH−C0〜6アルキレンであり、−C2〜6アルキレン、−O−C2〜6アルキレン、−S−C2〜6アルキレン及びNH−C2〜6アルキレンについては、アルキレン基の1個の炭素原子は、任意選択的にO、S若しくはNHで置換することができ;
R4aは、H、−C1〜6アルキル、C2〜6アルキニル、C1〜6アルキレン−O−C1〜4アルキル、C1〜6アルキレン−OH、C1〜6ハロアルキル、シクロアルキル、ヘテロシクロアルキル、C0〜3アルキレン−C3〜14シクロアルキル、C0〜3アルキレン−C2〜14ヘテロシクロアルキル、アリール、ヘテロアリール、C0〜3アルキレン−C6〜14アリールであり、又は
R5及びR6は、それぞれ独立して、H、ハロ、−C1〜6アルキル、−C2〜6アルキニル、−C1〜6アルキレン−O−C1〜4アルキル、−C1〜6アルキレン−OH、−C1〜6ハロアルキル、−C1〜6アルキレンアミン、−C0〜6アルキレン−アミド、−C0〜3アルキレン−C(O)OH、−C0〜3アルキレン−C(O)OC1〜4アルキル、−C1〜6アルキレン−O−アリール、−C0〜3アルキレン−C(O)C1〜4アルキレン−OH、シクロアルキル、ヘテロシクロアルキル、アリール、ヘテロアリール、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−C0〜3アルキレン−C6〜14アリール、−C0〜3アルキレン−C2〜14ヘテロアリール若しくはシアノであり、又はR5及びR6は、それらが結合している原子と共に4〜6員環を形成し;
R7は、H若しくはC1〜6アルキルであり、又はR7及びR5は、それらが結合している原子と共に4〜6員環を形成し;
R8は、−C1〜6アルキル、−C0〜3アルキレン−C6〜14アリール、−C0〜3アルキレン−C3〜14ヘテロアリール、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−C1〜6アルコキシ、−O−C0〜3アルキレン−C6〜14アリール、−O−C0〜3アルキレン−C3〜14ヘテロアリール、−O−C0〜3アルキレン−C3〜14シクロアルキル、−O−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−NH−C1〜8アルキル、−N(C1〜8アルキル)2、−NH−C0〜3アルキレン−C6〜14アリール、−NH−C0〜3アルキレン−C2〜14ヘテロアリール、−NH−C0〜3アルキレン−C3〜14シクロアルキル、−NH−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、ハロ、シアノ若しくはC1〜6アルキレン−アミンであり;
ここでRp、R2、R2a、R3、R4、R4a、R5、R6、R7及びR8置換基の何れかのヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、シクロアルキル、スピロシクロアルキル、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、C=O基を含むことができ、更にスピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含み得る;
ここでRp、R1、R2、R2a、R3、R4、R4a、L、R5、R6、R7及びR8置換基の何れかの−C1〜6アルキル、−C2〜6アルケニル、−C2〜6アルキニル及び−OC1〜6アルキルの何れかは、非置換であるか、又はOH、−OC1〜6アルキル、−C1〜6アルキル−O−C1〜6アルキル、ハロ、−O−ハロC1〜6アルキル、−CN、−NRaRb、−(NRaRbRc)n、−OSO2Ra、−SO2Ra、−(CH2CH2O)nCH3、−(=O)、−C(=O)、−C(=O)Ra、−OC(=O)Ra、−C(=O)ORa、−C(=O)NRaRb、−O−SiRaRbRc、−SiRaRbRc、−O−(3〜10員のヘテロシクロアルキル)、6〜12員のアリール若しくはヘテロアリール、5〜12員のスピロシクロアルキル若しくはスピロヘテロシクロアルキル、3〜12員のシクロアルケニル、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基から独立して選択される1、2若しくは3つのR9置換基によって置換されており、ヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、シクロアルキル、スピロシクロアルキル、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、C=O基を含むことができ、更にスピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含むことができ;
ここでRp、R1、R2、R2a、R3、R4、R4a、R5、R6、R7、R8及びR9置換基の何れかのアリール、ヘテロアリール、シクロアルキル及びヘテロシクロアルキル基は、非置換であるか、又はOH、ハロ、−NRcRd、−C1〜6アルキル、−OC1〜6アルキル、−C1〜6アルキル−OH、−C1〜6アルキル−O−C1〜6アルキル、C1〜6ハロアルキル、−O−ハロC1〜6アルキル、−SO2Rc、−CN、−C(=O)NRcRd、−C(=O)Rc、−OC(=O)Ra、−C(=O)ORc、6〜12員のアリール若しくはヘテロアリール、5〜12員のスピロシクロアルキル若しくはスピロヘテロシクロアルキル、3〜12員のシクロアルケニル、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基から独立して選択される1、2、3若しくは4つのR10置換基で置換されてよく、R10のヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、R10のシクロアルキル、スピロシクロアルキル及びスピロヘテロシクロアルキル基又はR10のヘテロシクロアルキル基はC=O基を含むことができ、更にスピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含むことができ;
ここで各Ra、Rb、Rc及びRdは、独立して水素、OH、−C1〜6アルキル、−(CH2CH2O)nCH3、−NR11R11、−C1〜6アルキル−NR11R11、フェニル、−C1〜6アルキル−C(=O)OH、−C1〜6アルキル−C(=O)−O−C1〜6アルキル、−C1〜6アルキル−3〜12員のシクロアルキル、−C1〜6アルキル−3〜12員のヘテロシクロアルキル、−C1〜6アルキル−6〜12員のヘテロアリール、6〜12員のアリール若しくはヘテロアリール、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基であり、Ra、Rb、Rc及びRdのヘテロアリール基、ヘテロシクロアルキル基、又はRa、Rb、Rc及びRdのC1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、Ra、Rb、Rc及びRdのシクロアルキル及びヘテロシクロアルキル基並びにRa、Rb、Rc及びRdの−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、二重結合を含むことができ、更にRa、Rb、Rc及びRdのシクロアルキル及びヘテロシクロアルキル基並びにRa、Rb、Rc及びRdの−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、C=O基を含有することができ;及び
Ra、Rb、Rc及びRdのアルキル、アリール、ヘテロアリール、シクロアルキル、ヘテロシクロアルキル基又はRa、Rb、Rc及びRdの−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、非置換であるか、又は1、2、3若しくは4つのR12置換基で置換することができ、各R12は、H、OH、ハロ、−C1〜6アルキル、N(CH3)2、−C1〜6ハロアルキル、C(=O)CH3、−C(=O)OCH3若しくは−C1〜6アルキル−O−C1〜6アルキルから独立して選択される]の構造を有する化合物;又は
その立体異性体、そのアトロプ異性体、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若しくはそのアトロプ異性体の薬学的に許容される塩を提供する。
式(Ia):
その立体異性体、そのアトロプ異性体、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若しくはそのアトロプ異性体の薬学的に許容される塩。
Rpは、−C1〜6アルキルである、実施形態1又は2の何れか1つに記載の化合物。
RPは、−CH3である、実施形態3に記載の化合物。
R1は、Hである、実施形態1〜4の何れか1つに記載の化合物。
R2は、非置換又は置換アリールである、実施形態1〜5の何れか1つに記載の化合物。
R2は、置換アリールである、実施形態6に記載の化合物。
R2は、フッ素化フェニルである、実施形態7に記載の化合物。
R3は、ハロである、実施形態1〜8の何れか1つに記載の化合物。
R3は、Clである、実施形態9に記載の化合物。
Lは、結合である、請求項11に記載の化合物。
環Aは、単環式の4〜7員環である、請求項11に記載の化合物。
Aは、非置換又は置換複素環である、請求項13に記載の化合物。
R5は、Hである、実施形態10に記載の化合物。
R6は、Hである、実施形態10に記載の化合物。
R8は、−C1〜6アルキル、−C0〜3アルキレン−C6〜14アリール又は−C0〜3アルキレン−C3〜14ヘテロアリールである、実施形態1〜18の何れか1つに記載の化合物。
R8は、−C1〜6アルキルである、実施形態19に記載の化合物。
R8は、−C6〜14アリールである、実施形態19に記載の化合物。
R8は、−C3〜14ヘテロアリールである、実施形態19に記載の化合物。
R8は、i−Pr、t−Bu、フェニル、ベンジル、OCH3、Cl、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、
式
又はその立体異性体、そのアトロプ異性体、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若しくはそのアトロプ異性体の薬学的に許容される塩。
薬学的に許容される塩の形態にある、実施形態1〜31の何れか1つに記載の化合物。
実施形態1〜32の何れか1つ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製剤。
細胞中のKRAS G12Cを阻害する方法であって、細胞と実施形態1〜32の何れか1つに記載の化合物又は実施形態33に記載の組成物とを接触させるステップを含む方法。
対象におけるがんを治療する方法であって、治療有効量の実施形態1〜32の何れか1つに記載の化合物又は実施形態33に記載の組成物を対象に投与するステップを含む方法。
がんは、肺がん、膵臓がん又は結腸直腸がんである、実施形態35に記載の方法。
がんは、肺ばんである、実施形態36に記載の方法。
がんは、非小細胞肺がんである、実施形態37に記載の方法。
がんは、膵臓がんである、実施形態36に記載の方法。
がんは、結腸直腸がんである、実施形態36に記載の方法。
それを必要とする患者に治療有効量の追加の医薬活性化合物を投与するステップを更に含む、実施形態35に記載の方法。
追加の薬学的に活性な化合物は、抗PD−1抗体である、実施形態41に記載の方法。
追加の薬学的に活性な化合物は、ニボルマブである、実施形態42に記載の方法。
追加の薬学的に活性な化合物は、ペンブロリズマブである、実施形態42に記載の方法。
追加の薬学的に活性な化合物は、AMG404である、実施形態42に記載の方法。
追加の薬学的に活性な化合物は、AMG−176である、実施形態41に記載の方法。
追加の薬学的に活性な化合物は、ダラツムマブである、実施形態41に記載の方法。
追加の薬学的に活性な化合物は、IMiDである、実施形態41に記載の方法。
対象におけるがんを治療するための、実施形態1〜32の何れか1つに記載の化合物の使用。
がんを治療するための医薬品の調製における、実施形態1〜32の何れか1つに記載の化合物。
がんは、固形腫瘍である、実施形態50に記載の化合物。
本明細書に開示した化合物は、多数の特定方法によって合成することができる。特定の合成経路を略述した実施例、及び下記の一般的スキームは、溶媒、濃度、試薬、保護基、合成ステップの順序、時間、温度等が、明確に技術及び通常の当業者の判断の範囲内で必要に応じて容易に修飾できるであろう通常の技術を備える合成化学者への指針を提供することが意図されている。
更に、本明細書では、例えば、希釈剤又は担体等の薬学的に許容される賦形剤と共に、本明細書に開示した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。化合物の投与については、以下でより詳細に記載する。
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、細胞と有効量の本明細書で開示した1種以上の化合物とを接触させるステップ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、証明することができる。非限定的な例としては、(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Kオフの増加又はGDPのKオフの減少;(d)pMEK、pERK又はpAKTレベルの減少等、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更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種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。
アトロプ異性体とリン異性体の混合物が記載されている表3の化合物に関して、以下のアッセイ条件を利用した:
Claims (51)
- 式(I):
E1及びE2は、それぞれ独立して、N若しくはCR1であり;
Rpは、独立して、H、ヒドロキシ、−C1〜6アルキル、ハロ、−C1〜4ハロアルキル、−C1〜4アルコキシ、−NH−C1〜4アルキル、−N(C1〜4アルキル)2、シアノ、−C2〜3アルケニル、−C2〜3アルキニル、−C3〜14シクロアルキル、−C2〜14ヘテロシクロアルキル、アリール若しくはヘテロアリールであり;
R1は、独立して、H、ヒドロキシ、−C1〜6アルキル、−C1〜6ハロアルキル、−C1〜6アルコキシ、−NH−C1〜6アルキル、−N(C1〜4アルキル)2、シアノ若しくはハロであり;
R2は、ハロ、−C1〜6アルキル、−C1〜6ハロアルキル、−OR2a、−N(R2a)2、−C2〜6アルケニル、−C2〜6アルキニル、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、アリール、ヘテロアリール、−C0〜3アルキレン−C6〜14アリール若しくは−C0〜3アルキレン−C2〜14ヘテロアリールであり、各R2aは、独立して、H、−C1〜6アルキル、−C1〜6ハロアルキル、−C3〜14シクロアルキル、−C2〜14ヘテロシクロアルキル、−C2〜6アルケニル、−C2〜6アルキニル、アリール若しくはヘテロアリールであり、又は2つのR2a置換基は、それらが結合している窒素原子と共に3〜7員環を形成し;
R3は、ハロ、−C1〜6アルキル、−C1〜6ハロアルキル、−C1〜6アルコキシ、C3〜6シクロアルキル、−C2〜14ヘテロシクロアルキル、−C2〜6アルケニル、−C2〜6アルキニル、アリール若しくはヘテロアリールであり;
R4は、
環Aは、単環式の4〜7員環、又は二環式の、架橋した、縮合した、若しくはスピロの6〜11員環であり;
Lは、結合、−C1〜6アルキレン、−O−C0〜6アルキレン、−S−C0〜6アルキレン若しくは−NH−C0〜6アルキレンであり、−C2〜6アルキレン、−O−C2〜6アルキレン、−S−C2〜6アルキレン及びNH−C2〜6アルキレンについては、前記アルキレン基の1個の炭素原子は、任意選択的にO、S若しくはNHで置換することができ;
R4aは、H、−C1〜6アルキル、C2〜6アルキニル、C1〜6アルキレン−O−C1〜4アルキル、C1〜6アルキレン−OH、C1〜6ハロアルキル、シクロアルキル、ヘテロシクロアルキル、C0〜3アルキレン−C3〜14シクロアルキル、C0〜3アルキレン−C2〜14ヘテロシクロアルキル、アリール、ヘテロアリール、C0〜3アルキレン−C6〜14アリールであり、又は
R5及びR6は、それぞれ独立して、H、ハロ、−C1〜6アルキル、−C2〜6アルキニル、−C1〜6アルキレン−O−C1〜4アルキル、−C1〜6アルキレン−OH、−C1〜6ハロアルキル、−C1〜6アルキレンアミン、−C0〜6アルキレン−アミド、−C0〜3アルキレン−C(O)OH、−C0〜3アルキレン−C(O)OC1〜4アルキル、−C1〜6アルキレン−O−アリール、−C0〜3アルキレン−C(O)C1〜4アルキレン−OH、シクロアルキル、ヘテロシクロアルキル、アリール、ヘテロアリール、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−C0〜3アルキレン−C6〜14アリール、−C0〜3アルキレン−C2〜14ヘテロアリール若しくはシアノであり、又はR5及びR6は、それらが結合している原子と共に4〜6員環を形成し;
R7は、H若しくはC1〜6アルキルであり、又はR7及びR5は、それらが結合している原子と共に4〜6員環を形成し;
R8は、−C1〜6アルキル、−C0〜3アルキレン−C6〜14アリール、−C0〜3アルキレン−C3〜14ヘテロアリール、−C0〜3アルキレン−C3〜14シクロアルキル、−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−C1〜6アルコキシ、−O−C0〜3アルキレン−C6〜14アリール、−O−C0〜3アルキレン−C3〜14ヘテロアリール、−O−C0〜3アルキレン−C3〜14シクロアルキル、−O−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、−NH−C1〜8アルキル、−N(C1〜8アルキル)2、−NH−C0〜3アルキレン−C6〜14アリール、−NH−C0〜3アルキレン−C2〜14ヘテロアリール、−NH−C0〜3アルキレン−C3〜14シクロアルキル、−NH−C0〜3アルキレン−C2〜14ヘテロシクロアルキル、ハロ、シアノ若しくはC1〜6アルキレン−アミンであり;
ここでRp、R2、R2a、R3、R4、R4a、R5、R6、R7及びR8置換基の何れかの前記ヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、前記シクロアルキル、スピロシクロアルキル、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、C=O基を含むことができ、前記スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含み得る;
ここで前記Rp、R1、R2、R2a、R3、R4、R4a、L、R5、R6、R7及びR8置換基の何れかの前記−C1〜6アルキル、−C2〜6アルケニル、−C2〜6アルキニル及び−OC1〜6アルキルの何れかは、非置換であるか、又はOH、−OC1〜6アルキル、−C1〜6アルキル−O−C1〜6アルキル、ハロ、−O−ハロC1〜6アルキル、−CN、−NRaRb、−(NRaRbRc)n、−OSO2Ra、−SO2Ra、−(CH2CH2O)nCH3、−(=O)、−C(=O)、
−C(=O)Ra、−OC(=O)Ra、−C(=O)ORa、−C(=O)NRaRb、−O−SiRaRbRc、−SiRaRbRc、−O−(3〜10員のヘテロシクロアルキル)、6〜12員のアリール若しくはヘテロアリール、5〜12員のスピロシクロアルキル若しくはスピロヘテロシクロアルキル、3〜12員のシクロアルケニル、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基から独立して選択される1、2若しくは3つのR9置換基によって置換されており、前記ヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、前記シクロアルキル、スピロシクロアルキル、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、C=O基を含むことができ、更に前記スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含むことができ;
ここで前記Rp、R1、R2、R2a、R3、R4、R4a、R5、R6、R7、R8及びR9置換基の何れかの前記アリール、ヘテロアリール、シクロアルキル及びヘテロシクロアルキル基は、非置換であるか、又はOH、ハロ、−NRcRd、−C1〜6アルキル、−OC1〜6アルキル、−C1〜6アルキル−OH、−C1〜6アルキル−O−C1〜6アルキル、C1〜6ハロアルキル、−O−ハロC1〜6アルキル、−SO2Rc、−CN、−C(=O)NRcRd、−C(=O)Rc、−OC(=O)Ra、−C(=O)ORc、6〜12員のアリール若しくはヘテロアリール、5〜12員のスピロシクロアルキル若しくはスピロヘテロシクロアルキル、3〜12員のシクロアルケニル、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基から独立して選択される1、2、3若しくは4つのR10置換基で置換されてよく、R10の前記ヘテロアリール、スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、R10の前記シクロアルキル、スピロシクロアルキル及びスピロヘテロシクロアルキル基又はR10の前記ヘテロシクロアルキル基はC=O基を含むことができ、更に前記スピロヘテロシクロアルキル及びヘテロシクロアルキル基は、S=O若しくはSO2を含むことができ;
ここで各Ra、Rb、Rc及びRdは、独立して水素、OH、−C1〜6アルキル、−(CH2CH2O)nCH3、−NR11R11、−C1〜6アルキル−NR11R11、フェニル、−C1〜6アルキル−C(=O)OH、−C1〜6アルキル−C(=O)−O−C1〜6アルキル、−C1〜6アルキル−3〜12員のシクロアルキル、−C1〜6アルキル−3〜12員のヘテロシクロアルキル、−C1〜6アルキル−6〜12員のヘテロアリール、6〜12員のアリール若しくはヘテロアリール、3〜12員の単環式若しくは二環式のシクロアルキル又は3〜12員の単環式若しくは二環式のヘテロシクロアルキル基であり、Ra、Rb、Rc及びRdの前記ヘテロアリール基、ヘテロシクロアルキル基、又はRa、Rb、Rc及びRdの前記C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、O、N若しくはSから独立して選択される1、2、3若しくは4個のヘテロ原子を有し、Ra、Rb、Rc及びRdの前記シクロアルキル及びヘテロシクロアルキル基並びにRa、Rb、Rc及びRdの前記−C1〜6アルキル−ヘテロシクロアルキル基の前記ヘテロシクロアルキル基は、二重結合を含むことができ、更にRa、Rb、Rc及びRdの前記シクロアルキル及びヘテロシクロアルキル基並びにRa、Rb、Rc及びRdの前記−C1〜6アルキル−ヘテロシクロアルキル基の前記ヘテロシクロアルキル基は、C=O基を含有することができ;及び
Ra、Rb、Rc及びRdの前記アルキル、アリール、ヘテロアリール、シクロアルキル、ヘテロシクロアルキル基又はRa、Rb、Rc及びRdの前記−C1〜6アルキル−ヘテロシクロアルキル基のヘテロシクロアルキル基は、非置換であるか、又は1、2、3若しくは4つのR12置換基で置換することができ、ここで各R12は、H、OH、ハロ、−C1〜6アルキル、N(CH3)2、−C1〜6ハロアルキル、C(=O)CH3、−C(=O)OCH3若しくは−C1〜6アルキル−O−C1〜6アルキルから独立して選択される]の構造を有する化合物;又は
その立体異性体、そのアトロプ異性体、その薬学的に許容される塩、前記その立体異性体の薬学的に許容される塩若しくは前記そのアトロプ異性体の薬学的に許容される塩。 - Rpは、−C1〜6アルキルである、請求項1又は2の何れか一項に記載の化合物。
- RPは、−CH3である、請求項3に記載の化合物。
- R1は、Hである、請求項1〜4の何れか一項に記載の化合物。
- R2は、非置換又は置換アリールである、請求項1〜5の何れか一項に記載の化合物。
- R2は、置換アリールである、請求項6に記載の化合物。
- R2は、フッ素化フェニルである、請求項7に記載の化合物。
- R3は、ハロである、請求項1〜8の何れか一項に記載の化合物。
- R3は、Clである、請求項9に記載の化合物。
- Lは、結合である、請求項11に記載の化合物。
- 環Aは、単環式の4〜7員環である、請求項11に記載の化合物。
- 環Aは、非置換又は置換複素環である、請求項13に記載の化合物。
- R5は、Hである、請求項10に記載の化合物。
- R6は、Hである、請求項10に記載の化合物。
- R8は、−C1〜6アルキル、−C0〜3アルキレン−C6〜14アリール又は−C0〜3アルキレン−C3〜14ヘテロアリールである、請求項1〜18の何れか一項に記載の化合物。
- R8は、−C1〜6アルキルである、請求項19に記載の化合物。
- R8は、−C6〜14アリールである、請求項19に記載の化合物。
- R8は、−C3〜14ヘテロアリールである、請求項19に記載の化合物。
- 薬学的に許容される塩の形態にある、請求項1〜31の何れか一項に記載の化合物。
- 請求項1〜32の何れか一項に記載の前記化合物及び薬学的に許容される賦形剤を含む医薬製剤。
- 細胞中のKRAS G12Cを阻害する方法であって、前記細胞と請求項1〜32の何れか一項に記載の化合物又は請求項33に記載の組成物とを接触させるステップを含む方法。
- 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1〜32の何れか一項に記載の化合物又は請求項33に記載の組成物を前記対象に投与するステップを含む方法。
- 前記がんは、肺がん、膵臓がん又は結腸直腸がんである、請求項35に記載の方法。
- 前記がんは、肺がんである、請求項36に記載の方法。
- 前記肺がんは、非小細胞肺がんである、請求項37に記載の方法。
- 前記がんは、膵臓がんである、請求項36に記載の方法。
- 前記がんは、結腸直腸がんである、請求項36に記載の方法。
- それを必要とする前記患者に治療有効量の追加の薬学的に活性な化合物を投与するステップを更に含む、請求項35に記載の方法。
- 前記追加の薬学的に活性な化合物は、抗PD−1抗体である、請求項41に記載の方法。
- 前記追加の薬学的に活性な化合物は、ニボルマブである、請求項42に記載の方法。
- 前記追加の薬学的に活性な化合物は、ペンブロリズマブである、請求項42に記載の方法。
- 前記追加の薬学的に活性な化合物は、AMG404である、請求項42に記載の方法。
- 前記追加の薬学的に活性な化合物は、AMG−176である、請求項41に記載の方法。
- 前記追加の薬学的に活性な化合物は、ダラツムマブである、請求項41に記載の方法。
- 前記追加の薬学的に活性な化合物は、IMiDである、請求項41に記載の方法。
- 対象におけるがんを治療するための、請求項1〜32の何れか一項に記載の化合物の使用。
- がんを治療するための医薬品の調製における、請求項1〜32の何れか一項に記載の化合物。
- 前記がんは、固形腫瘍である、請求項50に記載の化合物。
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WO2019213526A1 (en) | 2019-11-07 |
EP3788053B1 (en) | 2024-07-10 |
US20190336514A1 (en) | 2019-11-07 |
MA52496A (fr) | 2021-03-10 |
CA3099118A1 (en) | 2019-11-07 |
MX2020011582A (es) | 2020-11-24 |
EP3788053A1 (en) | 2021-03-10 |
JP7361722B2 (ja) | 2023-10-16 |
US11045484B2 (en) | 2021-06-29 |
AU2019262599B2 (en) | 2023-10-12 |
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