JP2022513971A - Kif18a阻害剤として有用なヘテロアリールアミド - Google Patents
Kif18a阻害剤として有用なヘテロアリールアミド Download PDFInfo
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- 229960000241 vandetanib Drugs 0.000 description 1
- 210000005167 vascular cell Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229940099039 velcade Drugs 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
- 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
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 229940053867 xeloda Drugs 0.000 description 1
- 235000020138 yakult Nutrition 0.000 description 1
- 229940055760 yervoy Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- 229960004276 zoledronic acid 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
- 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
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
X1は、N又はCR6であり、
X2は、N又はCR7であり、
X3は、N又はCR8であり、
X4は、N又はCR9であり、
X1、X2、X3、及びX4のうち3つ以下がNであり、
X2、X3、及びX4のうちのいずれかがNである場合、Lは-(C=O)-NR3-又は-NR3-(C=O)-であり、
X2、X3、及びX4の全てがNではない場合、Lは-(C=O)-NR3-であり、
R1は基-Z-R12であり、
式中、Zは-C0-4alk-、-NR11-、-NR11SO2-C0-4alk-、-SO2NR11-C0-4alk-、-NR11SO2NR11-、-NR11SO2NR11-C(=O)-O-、-C0-4alk-S(=O)(=NH)-、C0-4alk-NR11-S(=O)(=NH)、-C0-4alk-S-、-C0-4alk-S(=O)-、-C0-4alk-SO2-、-O-、-P-、-P(=O)、-P(=O)2、-(C=O)-、-(C=O)NR11-、又は-NR11(C=O)であるか、或いは、
基-Z-R12は-N=S(=O)-(R12)2であり、式中、2つのR12の対は、択一的にこれらのそれぞれに結合した硫黄原子と組み合わさって、0、1、2、又は3個のN原子、並びにO及びSから選択される0、1、又は2個の原子を含有する飽和又は部分飽和3、4、5、又は6員単環式環を形成することができ、
R2はハロ又は基-Y-R13であり、式中、Yは、-C0-4alk-、-N(C0-1alk)-C0-4alk-、-C(=O)NRaRa(C1-4alk)-、-O-C0-4alk-、-S-、-S=O、-S(=O)2-、-SO2N(C0-1alk)-C0-4alk-、-N(C0-1alk)-SO2-C0-4alk-、-C0-4alk-S(=O)(=NH)-、-(C=O)-、-C0-4alk-(C=O)-O-であるか、或いは、
基-Y-R13は-N=S(=O)-(R13)2であり、式中、2つのR13の対は、択一的にこれらのそれぞれに結合した硫黄原子と組み合わさって、0、1、2、又は3個のN原子、並びにO及びSから選択される0、1、又は2個の原子を含有する飽和又は部分飽和3、4、5、又は6員単環式環を形成することができ、
R3はH、メチル、又はエチルであり、
R4はH、ハロ、C1-4alk、又はC1-4ハロalkであり、
R5はH、ハロ、C1-8alk、又はC1-4ハロalkであり、
R6はH、ハロ、CN、-O-C0-6alk-、R6a又はR6bであり、
R7はH、ハロ、C1-4alk、又はC1-4ハロalkであり、
R8はH、ハロ、C1-8alk、又はC1-4ハロalkであり、
R9はH、ハロ、C1-4alk、又はC1-4ハロalkであり、
Rxは、
R10a、R10b、R10c、R10d、R10e、R10f、R10g、R10h、R10i、及びR10jのそれぞれはH、ハロ、R10k、又はR10lであるか、
或いは、R10a及びR10bの対、R10c及びR10dの対、R10e及びR10fの対、R10g及びR10hの対、又はR10i及びR10jの対はそれぞれ独立して、これらのそれぞれに結合した炭素原子と組み合わさって、Rx環に対してスピロである飽和又は部分飽和3、4、5、6員単環式環を形成し得、上記の3、4、5、6員単環式環は、0、1、2、又は3個のN原子、並びにO及びSから選択される0、1、又は2個の原子を含有し、更に、前記3、4、5、6員単環式環は、F、Cl、Br、C1-6alk、C1-4ハロalk、-ORa、-OC1-4ハロalk、CN、-NRaRa、又はオキソから選択される0、1、2、又は3個の基によって置換され、
R11は、H又はC1-8-alkであり、
R12はH、ハロ、R12a、又はR12bであり、
R13はR13a又はR13bであり、
R6a、R10k、R12a、及びR13aは、独立して、各場合において、F、Cl、Br、C1-6alk、C1-4ハロalk、-ORa、-OC1-4ハロalk、CN、-C(=O)Rb、-C(=O)ORa、-C(=O)NRaRa、-C(=NRa)NRaRa、-OC(=O)Rb、-OC(=O)NRaRa、-OC2-6alkNRaRa、-OC2-6alkORa、-SRa、-S(=O)Rb、-S(=O)2Rb、-S(=O)2NRaRa、-NRaRa、-N(Ra)C(=O)Rb、-N(Ra)C(=O)ORb、-N(Ra)C(=O)NRaRa、-N(Ra)C(=NRa)NRaRa、-N(Ra)S(=O)2Rb、-N(Ra)S(=O)2NRaRa、-NRaC2-6alkNRaRa、-NRaC2-6alkORa、-C1-6alkNRaRa、-C1-6alkORa、-C1-6alkN(Ra)C(=O)Rb、-C1-6alkOC(=O)Rb、-C1-6alkC(=O)NRaRa、-C1-6alkC(=O)ORa、R14、及びオキソから選択される0、1、2、又は3個の基によって置換されている、0、1、2、又は3個のN原子、並びにO及びSから選択される0、1、又は2個の原子を含有する、飽和、部分飽和、又は不飽和3、4、5、6、若しくは7員単環式環又は4、5、6、7、8、9、10、11、若しくは12員二環式環からなる群から選択され、
R6b、R10l、R12b、及びR13bは、独立して、各場合において、F、Cl、Br、-C(=O)ORa、-ORa、-C1-2ハロalk、-OC1-4ハロalk、CN、NH2、NH(CH3)、又はN(CH3)2から選択される0、1、2、3、4、又は5個の基によって置換されている、C1-6alkからなる群から選択され、
R14は、F、Cl、Br、C1-6alk、C1-4ハロalk、-ORa、-OC1-4ハロalk、CN、-C(=O)Rb、-C(=O)ORa、-C(=O)NRaRa、-C(=NRa)NRaRa、-OC(=O)Rb、-OC(=O)NRaRa、-OC2-6alkNRaRa、-OC2-6alkORa、-SRa、-S(=O)Rb、-S(=O)2Rb、-S(=O)2NRaRa、-NRaRa、-N(Ra)C(=O)Rb、-N(Ra)C(=O)ORb、-N(Ra)C(=O)NRaRa、-N(Ra)C(=NRa)NRaRa、-N(Ra)S(=O)2Rb、-N(Ra)S(=O)2NRaRa、-NRaC2-6alkNRaRa、-NRaC2-6alkORa、-C1-6alkNRaRa、-C1-6alkORa、-C1-6alkN(Ra)C(=O)Rb、-C1-6alkOC(=O)Rb、-C1-6alkC(=O)NRaRa、-C1-6alkC(=O)ORa、及びオキソから選択される0、1、2、又は3個の基によって置換されている、0、1、2、又は3個のN原子、並びにO及びSから選択される0、1、又は2個の原子を含有する、飽和、部分飽和、又は不飽和3、4、5、6、若しくは7員単環式環又は4、5、6、7、8、9、10、11、若しくは12員二環式環からなる群から選択され、
Raは、独立して、各場合において、H又はRbであり、
Rbは、独立して、各場合において、C1-6alk、フェニル、又はベンジルであり、C1-6alkは、ハロ、-OH、-OC1-4alk、-NH2、-NHC1-4alk、-OC(=O)C1-4alk、又は-N(C1-4alk)C1-4alkから選択される0、1、2、又は3個の置換基によって置換され、フェニル又はベンジルは、ハロ、C1-4alk、C1-3ハロalk、-OH、-OC1-4alk、-NH2、-NHC1-4alk、-OC(=O)C1-4alk、又は-N(C1-4alk)C1-4alkから選択される0、1、2、又は3個の置換基によって置換されている。
R13は、F、Cl、Br、-OH、-OC1-4ハロalk、又はCNから選択される0、1、2、3、4、又は5個の基によって置換されている、C1-6alkである。
(a)F、Br;
(b)基-Y-R13であって、式中、Yは不在若しくはSO2であり、R13は、モルホリニル、オキサゾリジニル、オキサゾリル、ピロリジニル、ピペリジニル、アゼチジニル、ジヒドロピラニル、ジヒドロピリジニル、ピペラジニル、テトラヒドロピラニル、
各前記環は、F、Cl、Br、メチル、エチル、-OH、-OCH3、CH2OH、NH2、NH(CH3)若しくはオキソから選択される0、1、2、若しくは3個の基によって置換されている、基-Y-R13;又は
(c)基-Y-R13であって、式中、YはNH若しくは-SO2NH-であり、R13は、F、Cl、Br、メチル、CF3、又は-OHから選択される0、1、2、3、4、若しくは5個の基によって置換されている、C1-6alkである、基-Y-R13である。
各上記の環は、F、Cl、Br、メチル、CF3、-OH、-OCHF2、CN、及びオキソから選択される0、1、2、又は3個の基によって置換されている、基-Y-R13であるか、又は基-Y-R13であって、式中、YはNH、-O-、-O-(CH2)-、-O-(CH2)-(CH2)-、若しくは-O-(CH2)-(CH2)-(CH2)-であり、R13は
基N(Ra)Raなどとしては、2つのRa基が共に、任意選択的にN、O、又はS原子を含む環を形成する置換基が挙げられ、これとしては、
更に、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。化合物の投与について、以下でより詳細に説明する。
本開示は、一般にはMTベースのKIF18A調節活性、具体的には阻害活性を有する化合物を提供する。本発明の一実施形態では、対象においてKIF18Aタンパク質を調節する方法が提供され、方法は、対象に有効投薬量の式Iの化合物を投与することを含む。そのため、本発明の化合物は、無制御な細胞成長、異常な細胞周期調整、中心体異常(構造的及び/又は数的な、フラグメンテーション)を含む細胞増殖障害の治療に使用され得る。余分な中心体(>2)の蓄積を伴うその他の疾患又は障害としては、ヒトパピローマウイルス(HPV)関連新生物形成を含むHPV感染症が挙げられる。化合物はまた、繊毛関連疾患、及び男性用避妊薬として使用され得る半数体生殖細胞集団を切除することにも有用である。
本発明の化合物は、単独の活性医薬品として服用又は投与することができるが、これらは、1つ以上の本発明の化合物と併用してもよく、又は他の薬剤と組み合わせて用いてもよい。併用剤として投与する場合、治療剤を同時若しくは異なる時点で逐次的に投与される別個の組成物として製剤化してもよく、又は治療剤を単一の組成物として与えてもよい。
略語:本明細書では、下記の略語を使用することができる:
特に指示しない限り、これらの化合物を調製するのに用いられる出発物質及び試薬は、Aldrich Chemical Co.,(Milwaukee,Wis.)、Bachem(Torrance,Calif.)、若しくはSigma(St.Louis,Mo.)などの市販業者から入手可能であるか、又は、Fieser and Fieser’s Reagents for Organic Synthesis,Volumes1-17(John Wiley and Sons,1991);Rodd’s Chemistry of Carbon Compounds,Volumes1-5 and Supplementals(Elsevier Science Publishers,1989);Organic Reactions,Volumes1-40(John Wiley and Sons,1991)、March’s Advanced Organic Chemistry,(John Wiley and Sons,4th Edition)、及びLarock’s Comprehensive Organic Transformations(VCH Publishers Inc.,1989)などの参考文献に記載される手順に従う、当業者に既知の方法によって調製されるかのいずれかである。これらのスキームは、本発明の化合物を合成することのできるいくつかの方法を例示するに過ぎず、これらのスキームに様々な修正が実施可能であり、且つ、本開示を参照した当業者に示唆されるであろう。反応の出発物質及び中間体並びに最終生成物は、所望に応じて、濾過、蒸留、結晶化、クロマトグラフィーなどが挙げられるがこれらに限定されない従来技術を用いて単離及び精製され得る。こうした材料は、物理定数及びスペクトルデータを含む従来の手段を用いて特性決定され得る。
工程1:環Ar1化合物の調製。
工程2:環Ar2化合物の調製。
工程3:環Ar1化合物の環Ar2化合物へのカップリング。
別の実施形態では、本明細書で定義される、下記の式(Id)を有する式(I)の化合物:
中間体1:(S)-6-(2-メチルモルホリノ)ピリジン-2-アミン。
この化合物は、中間体32に関して上述したものと類似する様式で調製した。1H NMR(400MHz,クロロホルム-d)δ ppm 1.50-1.70(m,3H),1.81-1.88(m,2H),2.15(s,3H),3.34-3.56(m,3H),3.61-3.67(m,1H),3.87(dt,J=6.48,3.29Hz,1H),4.04-4.21(m,2H),5.72(s,1H),5.90(s,1H).m/z(ESI):208.0(M+H)+.
この化合物は、中間体36に関して上述したものと類似する様式で調製した。m/z(ESI):206.0(M+H)+.
この化合物は、6-アミノ-N-(tert-ブチル)ピリジン-2-スルホンアミド(中間体31)に関して説明したものと類似する様式で調製した。
m/z(ESI):244.0(M+H)+.
中間体41:2-(6-アザスピロ[2.5]オクタン-6-イル)-6-(1,1,1-トリフルオロ-2-ヒドロキシプロパン-2-イル)ニコチン酸。
実施例100:5-((1-ヒドロキシ-2-メチルプロパン-2-イル)アミノ)-N-(6-(ピペリジン-1-イルスルホニル)ピリジン-2-イル)-3-(6-アザスピロ[2.5]オクタン-6-イル)ピラジン-2-カルボキサミド。
この化合物は、実施例113に関して記載される手順を用いて調製した。
この化合物は、実施例113に関して記載される手順を用いて調製した。
この化合物は、実施例134に関して上述された方法に従い調製した。
この化合物は、実施例116に関して記載したものと類似の方法で調製した。
この化合物は、実施例113に関して記載したものと類似の方法で調製した。
この化合物は、実施例162に関して記載したものと類似の方法で調製した。
これらの化合物は、実施例194及び195に関して上述したものと類似する様式で合成された。
この化合物は、実施例193に関して記載されたものと類似する様式で合成した。m/z(ESI):556.2(M+H)+.
この化合物は、実施例104に関して上述したものと類似する様式で調製した。
1H NMR(400MHz,DMSO-d6):δ ppm 12.51(s,1H),7.95(d,J=8.7Hz,1H),7.72(dd,J=8.5,2.4Hz,1H),7.53(dd,J=12.8,8.5Hz,1H),6.82(s,1H),6.44(d,J=8.7Hz,1H),4.82(t,J=5.7Hz,1H),3.79-3.94(m,3H),3.62-3.73(m,2H),3.60(d,J=5.7Hz,2H),3.05(t,J=5.5Hz,4H),2.91-2.99(m,1H),2.60-2.70(m,1H),1.70(s,4H),1.36(s,6H),1.16(d,J=6.2Hz,3H),0.37(s,4H).m/z(ESI):513.3(m+H)+.
下記のアッセイは、本発明の例示的な化合物を試験するのに使用した。下記の手順に従い試験されたこれらの実施例のデータを、下記の表Aに示す。
Claims (40)
- 式Iの化合物:
X1は、N又はCR6であり、
X2は、N又はCR7であり、
X3は、N又はCR8であり、
X4は、N又はCR9であり、
X1、X2、X3、及びX4のうちの3つ以下がNであり、
X2、X3、及びX4のうちのいずれかがNである場合、Lは、-(C=O)-NR3-又は-NR3-(C=O)-であり、
X2、X3、及びX4の全てがNではない場合、Lは、-(C=O)-NR3-であり、
R1は、基-Z-R12であり、
式中、Zは、-C0-4alk-、-NR11-、-NR11SO2-C0-4alk-、-SO2NR11-C0-4alk-、-NR11SO2NR11-、-NR11SO2NR11-C(=O)-O-、-C0-4alk-S(=O)(=NH)-、C0-4alk-NR11-S(=O)(=NH)、-C0-4alk-S-、-C0-4alk-S(=O)-、-C0-4alk-SO2-、-O-、-P-、-P(=O)、-P(=O)2、-(C=O)-、-(C=O)NR11-、又は-NR11(C=O)であるか、或いは、
基-Z-R12は、-N=S(=O)-(R12)2であり、式中、2つのR12の対は、択一的にこれらのそれぞれに結合した硫黄原子と組み合わさって、0、1、2、又は3個のN原子、並びにO及びSから選択される0、1、又は2個の原子を含有する、飽和又は部分飽和3、4、5、又は6員単環式環を形成することができ、
R2は、ハロ又は基-Y-R13であり、式中、Yは、-C0-4alk-、-N(C0-1alk)-C0-4alk-、-C(=O)NRaRa(C1-4alk)-、-O-0-4alk-、-S-、-S=O、-S(=O)2-、-SO2N(C0-1alk)-C0-4alk-、-N(C0-1alk)-SO2-C0-4alk-、-C0-4alk-S(=O)(=NH)-、-(C=O)-、-C0-4alk-(C=O)-O-であるか、或いは、
基-Y-R13は、-N=S(=O)-(R13) 2であり、式中、2つのR13の対は、択一的にこれらのそれぞれに結合した硫黄原子と組み合わさって、0、1、2、又は3個のN原子、並びにO及びSから選択される0、1、又は2個の原子を含有する、飽和又は部分飽和3、4、5、又は6員単環式環を形成することができ、
R3は、H、メチル、又はエチルであり、
R4は、H、ハロ、C1-4alk、又はC1-4ハロalkであり、
R5は、H、ハロ、C1-8alk、又はC1-4ハロalkであり、
R6は、H、ハロ、CN、-O-C0-6alk-、R6a又はR6bであり、
R7は、H、ハロ、C1-4alk、又はC1-4ハロalkであり、
R8は、H、ハロ、C1-8alk、又はC1-4ハロalkであり、
R9は、H、ハロ、C1-4alk、又はC1-4ハロalkであり、
Rxは、
R10a、R10b、R10c、R10d、R10e、R10f、R10g、R10h、R10i、及びR10jのそれぞれは、H、ハロ、R10k、又はR10lであるか、
或いは、R10a及びR10bの対、R10c及びR10dの対、R10e及びR10fの対、R10g及びR10hの対、又はR10i及びR10jの対のそれぞれは、独立して、これらのそれぞれに結合した炭素原子と組み合わさって、Rx環に対してスピロである飽和又は部分飽和3、4、5、6員単環式環を形成することができ、前記3、4、5、6員単環式環は、0、1、2、又は3個のN原子、並びにO及びSから選択される0、1、又は2個の原子を含有し、更に、前記3、4、5、6員単環式環は、F、Cl、Br、C1-6alk、C1-4ハロalk、-ORa、-OC1-4ハロalk、CN、NRaRa、又はオキソから選択される0、1、2、又は3個の基によって置換され、
R11は、H又はC1-8alkであり、
R12は、H、ハロ、R12a、又はR12bであり、
R13は、R13a又はR13bであり、
R6a、R10k、R12a、及びR13aは、独立して、各場合において、F、Cl、Br、C1-6alk、C1-4ハロalk、-ORa、-OC1-4ハロalk、CN、-C(=O)Rb、-C(=O)ORa、-C(=O)NRaRa、-C(=NRa)NRaRa、-OC(=O)Rb、-OC(=O)NRaRa、-OC2-6alkNRaRa、-OC2-6alkORa、-SRa、-S(=O)Rb、-S(=O)2Rb、-S(=O)2NRaRa、-NRaRa、-N(Ra)C(=O)Rb、-N(Ra)C(=O)ORb、-N(Ra)C(=O)NRaRa、-N(Ra)C(=NRa)NRaRa、-N(Ra)S(=O)2Rb、-N(Ra)S(=O)2NRaRa、-NRaC2-6alkNRaRa、-NRaC2-6alkORa、-C1-6alkNRaRa、-C1-6alkORa、-C1-6alkN(Ra)C(=O)Rb、-C1-6alkOC(=O)Rb、-C1-6alkC(=O)NRaRa、-C1-6alkC(=O)ORa、R14、及びオキソから選択される0、1、2、又は3個の基によって置換されている、0、1、2、又は3個のN原子、並びにO及びSから選択される0、1、又は2個の原子を含有する、飽和、部分飽和、又は不飽和3、4、5、6、若しくは7員単環式環又は4、5、6、7、8、9、10、11、若しくは12員二環式環からなる群から選択され、
R6b、R10l、R12b、及びR13bは、独立して、各場合において、F、Cl、Br、-C(=O)ORa、-ORa、-C1-2ハロalk、-OC1-1ハロalk、CN、NH2、NH(CH3)、又はN(CH3)2から選択される0、1、2、3、4、又は5個の基によって置換されている、C1-6alkからなる群から選択され、
R14は、F、Cl、Br、C1-6alk、C1-4ハロalk、-ORa、-OC1-4ハロalk、CN、-C(=O)Rb、-C(=O)ORa、-C(=O)NRaRa、-C(=NRa)NRaRa、-OC(=O)Rb、-OC(=O)NRaRa、-OC2-6alkNRaRa、-OC2-6alkORa、-SRa、-S(=O)Rb、-S(=O)2Rb、-S(=O)2NRaRa、-NRaRa、-N(Ra)C(=O)Rb、-N(Ra)C(=O)ORb、-N(Ra)C(=O)NRaRa、-N(Ra)C(=NRa)NRaRa、-N(Ra)S(=O)2Rb、-N(Ra)S(=O)2NRaRa、-NRaC2-6alkNRaRa、-NRaC2-6alkORa、-C1-6alkNRaRa、-C1-6alkORa、-C1-6alkN(Ra)C(=O)Rb、-C1-6alkOC(=O)Rb、-C1-6alkC(=O)NRaRa、-C1-6alkC(=O)ORa、及びオキソから選択される0、1、2、又は3個の基によって置換されている、0、1、2、又は3個のN原子並びにO及びSから選択される0、1、又は2個の原子を含有する、飽和、部分飽和、又は不飽和3、4、5、6、若しくは7員単環式環又は4、5、6、7、8、9、10、11、若しくは12員二環式環からなる群から選択され、
Raは、独立して、各場合において、H又はRbであり、
Rbは、独立して、各場合において、C1-6alk、フェニル、又はベンジルであり、前記C1-6alkは、ハロ、-OH、-OC1-6alk、-NH2、-NHC1-4alk、-OC(=O)C1-4alk、又は-N(C1-4alk)C1-4alkから選択される0、1、2、又は3個の置換基によって置換され、前記フェニル又はベンジルは、ハロ、C1-4alk、C1-3ハロalk、-OH、-OC1-4alk、-NH2、-NHC1-4alk、-OC(=O)C1-4alk、又は-N(C1-4alk)C1-4alkから選択される0、1、2、又は3個の置換基によって置換されている、前記式Iの化合物又は任意のその薬学的に許容される塩。 - R3は、H又はメチルである、請求項1~7のいずれか一項に記載の化合物。
- R10c、R10d、R10e、R10f、R10g、R10h、R10i、及びR10jのそれぞれが、H、ハロ、C1-6alk、又はC1-4ハロalkであり、R10a及びR10bの対のそれぞれが、これらのそれぞれに結合した炭素原子と組み合わさって、Rx環に対してスピロである飽和3、4、又は5員単環式環を形成し、前記環は、0、1、2、又は3個のN原子、並びにO及びSから選択される0又は1個の原子を含有する、請求項1~8のいずれか一項に記載の化合物。
- R10c、R10d、R10e、R10f、R10g、R10h、R10i、及びR10jのそれぞれが、H、メチル、又はエチルであり、R10a及びR10bの対のそれぞれが、これらのそれぞれ結合した炭素原子と組み合わさって、Rx環に対してスピロであるシクロプロピル、シクロブチル、又はシクロペンチル環を形成する、請求項1~9のいずれか一項に記載の化合物。
- Zは、不在、-NH-、-NHSO2-、-O-、-SO2NH-、-S(=O)(=NH)-、-CH2-S(=O)(=NH)-、-SO2-、-CH2-SO2、又はCH3(CH)-SO2である、請求項1~11のいずれか一項に記載の化合物。
- R12は、a)H、(b)F、(c)F、Cl、Br、-CF3、-C(=O)CH3、-OH、-OCH3、-NH2、シクロプロピル、シクロプロピルメタノール、若しくは3-(トリフルオロメチル)-3H-ジアジリニルから選択される0、1、2、若しくは3個の基によって置換されている、C1-6alk、又は(d)F、Cl、Br、メチル、エチル、-CF3、-C1-6alkOH、-OH、-OCH3、-NH2、若しくはオキソから選択される0、1、2、若しくは3個の基によって置換されている、0、1、2、若しくは3個のN原子、並びにO及びSから選択される0若しくは1個の原子を含有する、飽和、部分飽和、若しくは不飽和3、4、5、6、若しくは7員単環式環から選択される、請求項1~12のいずれか一項に記載の化合物。
- R12は、シクロプロピル、シクロブチル、シクロペンチル、オキセタニル、アゼチジニル、オキサゾリジニル、1,3-ジオキソラニル、又はピロリジニルから選択される、請求項1~13のいずれか一項に記載の化合物。
- R1は、基-Z-R12であり、Zは、-NHSO2-又は-SO2NH-であり、R12は、シクロプロピルであるか、或いはR12は、0、1、2、又は3個のOH基によって置換されているC1-6alkである、請求項1~15のいずれか一項に記載の化合物。
- R1は、基-Z-R12であり、Zは、-NHSO2-であり、R12は、-CH2-CH2-OHである、請求項1~16のいずれか一項に記載の化合物。
- R2は、基-Y-R13であり、Yは、不在、-NH-、又は-NHSO2-であり、
R13は、F、Cl、Br、メチル、エチル、CF3、CH2OH、-OH、-OCH3、-NH2、-NH(CH3)、及びオキソから選択される0、1、2、又は3個の基によって置換されている、0、1、2、又は3個のN原子、並びにO及びSから選択される0又は1個の原子を含有する、飽和、部分飽和、又は不飽和3、4、5、6、若しくは7員単環式環又は8、9、10、11、若しくは12員二環式環であるか、或いは、
R13は、F、Cl、Br、-OH、-OC1-4ハロalk、又はCNから選択される0、1、2、3、4、又は5個の基によって置換されている、C1-6alkである、請求項1~17のいずれか一項に記載の化合物。 - R2は、飽和5又は6員単環式環であり、各前記環は、1又は2個のN原子及び0又は1個のO原子を含有し、各前記環は、F、Cl、Br、C1-6alk、C1-4ハロalk、-OH、-OC1-4ハロalk、CN、R14、及びオキソから選択される0、1、2、又は3個の基によって置換されている、請求項1~18のいずれか一項に記載の化合物。
- R2は、
(a)F、Br;
(b)基-Y-R13であって、式中、Yは、不在若しくはSO2であり、R13は、モルホリニル、オキサゾリジニル、オキサゾリル、ピロリジニル、ピペリジニル、アゼチジニル、ジヒドロピラニル、ジヒドロピリジニル、ピペラジニル、テトラヒドロピラニル、
(c)基-Y-R13であって、式中、Yは、NH若しくは-SO2NH-であり、R13は、F、Cl、Br、メチル、CF3、又は-OHから選択される0、1、2、3、4、若しくは5個の基によって置換されている、C1-6alkである、前記基-Y-R13である、請求項1~19のいずれか一項に記載の化合物。 - R2は、基-Y-R13であって、式中、Yは、不在であり、R13は、モルホリニル、ピペリジニル、アゼチジニル、ピロリジニル、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、ピペラジニル、テトラヒドロフラニル、
-O-(CH2)-(CH2)-(CH2)-であり、R13は、
- R2は、F、Cl、Br、メチル、CF3、-OH、-OCHF2、CN、又はオキソから選択される0、1、2、又は3個の基によって置換されている、モルホリニル又はピペリジニルである、請求項1~22のいずれか一項に記載の化合物。
- R2は、1、2、又は3個のメチル基によって置換されているモルホリニルである、請求項1~23のいずれか一項に記載の化合物。
- R2は、1、2、又は3個のフルオロ基によって置換されているピペリジニルである、請求項1~24のいずれか一項に記載の化合物。
- R4は、H又はハロである、請求項1~25のいずれか一項に記載の化合物。
- R5は、Hである、請求項1~26のいずれか一項に記載の化合物。
- R6は、H又はFである、請求項1~27のいずれか一項に記載の化合物。
- R7は、(a)H;(b)F、Cl、Br、-OH、-OCH3、若しくはシクロプロピルから選択される0、1、2、若しくは3個の基によって置換されている、C1-6alk;又は(c)F、Cl、Br、C1-6alk、C1-4ハロalk、-C1-6alkOH、-OH、-OCH3、-NH2、若しくはオキソから選択される0、1、2、若しくは3個の基によって置換されている、0、1、2、若しくは3個のN原子、並びにO及びSから選択される0若しくは1個の原子を含有する、飽和、部分飽和、若しくは不飽和3、4、5、6、若しくは7員単環式環から選択される、請求項1~28のいずれか一項に記載の化合物。
- R6は、Hである、請求項1~29のいずれか一項に記載の化合物。
- R7は、Hである、請求項1~30のいずれか一項に記載の化合物。
- R8は、Hである、請求項1~31のいずれか一項に記載の化合物。
- R9は、Hである、請求項1~32のいずれか一項に記載の化合物。
- 請求項1~34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、及び薬学的に許容される希釈剤又は担体を含む、医薬組成物。
- KIF18A阻害剤で治療され得る症状を治療するための方法であって、治療有効量の請求項1~34のいずれか一項に記載の化合物、又は請求項35に記載の組成物を、それを必要とする患者に投与することを含む、方法。
- 前記症状は、(a)膀胱がん、子宮内膜がん、肺扁平上皮がん、乳がん、結腸がん、腎臓がん、肝臓がん、肺がん、小細胞肺がん、食道がん、胆嚢がん、脳がん、頭頚部がん、卵巣がん、膵臓がん、胃がん、子宮頚がん、甲状腺がん、前立腺がん、及び皮膚がんのがんから選択される固形腫瘍又は血液由来の腫瘍、(b)白血病、急性リンパ性白血病、急性リンパ芽球性白血病、B細胞リンパ腫、T細胞リンパ腫、ホジキンリンパ腫、非ホジキンリンパ腫、毛様細胞リンパ腫、及びバーキットリンパ腫から選択されるリンパ系の造血器腫瘍、(c)急性及び慢性骨髄性白血病、骨髄異形成症候群、並びに前骨髄球性白血病から選択される骨髄細胞系列の造血器腫瘍、(d)線維肉腫及び横紋筋肉腫から選択される間葉起源の腫瘍、(e)星状細胞腫、神経芽細胞腫、神経膠腫、及び神経鞘腫から選択される中枢及び末梢神経系の腫瘍、又は(f)黒色腫、精上皮腫、奇形腫、骨肉腫、色素性乾皮症、角化棘細胞腫、甲状腺濾胞がん、又はカポジ肉腫からなる群から選択されるがんである、請求項36に記載の方法。
- 対象における固形腫瘍のサイズを減少させる方法であって、治療有効量の請求項1~34のいずれか一項に記載の化合物、又は請求項35に記載の組成物を、それを必要とする前記対象に投与することを含む、方法。
- 対象における細胞増殖障害を治療する方法であって、治療有効量の請求項1~34のいずれか一項に記載の化合物、又は請求項35に記載の組成物を、それを必要とする前記対象に投与することを含む、方法。
- 細胞でのKIF18Aを阻害する方法であって、前記細胞を、請求項1~34のいずれか一項に記載の化合物、若しくはその薬学的に許容される塩、又は請求項35に記載の組成物と接触させることを含む、方法。
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MX2021007157A (es) | 2021-08-16 |
AU2019401495A1 (en) | 2021-06-24 |
US20220002311A1 (en) | 2022-01-06 |
MA54547A (fr) | 2022-03-30 |
EP3898592A1 (en) | 2021-10-27 |
CA3123044A1 (en) | 2020-06-25 |
WO2020132653A1 (en) | 2020-06-25 |
EP3898592B1 (en) | 2024-10-09 |
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