JP7407196B2 - Kif18a阻害剤 - Google Patents
Kif18a阻害剤 Download PDFInfo
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- JP7407196B2 JP7407196B2 JP2021534715A JP2021534715A JP7407196B2 JP 7407196 B2 JP7407196 B2 JP 7407196B2 JP 2021534715 A JP2021534715 A JP 2021534715A JP 2021534715 A JP2021534715 A JP 2021534715A JP 7407196 B2 JP7407196 B2 JP 7407196B2
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61K31/33—Heterocyclic compounds
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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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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- C—CHEMISTRY; METALLURGY
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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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
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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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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Description
X1はN又は-CR6であり、
R1は-CN、又は基-Z-R12であり、式中、Zは-C0-4alk-、-NR11-、-NR11SO2-、-SO2NR11-、-NR11-S(=O)(=NH)、-S(=O)(=NH)-、-S-、-S(=O)-、-SO2-、C0-4alk-O-、-(C=O)-、-(C=O)NR11-、-C=N(OH)-、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、二者択一的にこれらのそれぞれに付着した硫黄原子と結合して、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、-SO2NR13、又は-S(=O)(=NH)-であり、
R3はH、C1-4alk、又はC1-4haloalkであり、
R4はH、ハロ、R4a、又はR4bであり、
R5はH、ハロ、C1-8alk、又はC1-4haloalkであり、
R6はH、ハロ、C1-8alk、C1-8haloalk、-O-C1-8alk、又は-O-R6aであり、式中、R6a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個の原子を含有する飽和又は部分飽和3、4、5、又は6員単環式環であり、
R7はH、ハロ、C1-8alk、又はC1-4haloalkであり、
R8はH、ハロ、C1-8alk、C1-4haloalk、-OH、-O-R8a、又は-O-R8bであり、
R9はH、ハロ、C1-8alk、又はC1-4haloalk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、二者択一的に、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付着した炭素原子と結合して、Rx環に対する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、上記の3、4、5、6員単環式環は、F、Cl、Br、C1-6alk、C1-4haloalk、-ORa、-OC1-4haloalk、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、R11a、又はR11bであり、
R12はH、R12a、又はR12bであり、
R13はR13a又はR13bであり、
R4a、R8a、R10k、R11a、R12a、及びR13aは、独立して、各場合において、F、Cl、Br、C1-6alk、C1-4haloalk、-ORa、-OC1-4haloalk、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、
R4b、R8b、R10l、R11b、R12b、及びR13bは、独立して、各場合において、F、Cl、Br、-ORa、-OC1-4haloalk、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るC1-6alkからなる群から選択され、
R14は、独立して、各場合において、F、Cl、Br、C1-6alk、C1-4haloalk、-ORa、OC1-4haloalk、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、C1-3haloalk、-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る。
(a)H、
(b)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、オキシラニル、オキセタニル、テトラヒドロフラニル、アゼチジニル、イミダゾリル、モルホリニル、ピロリジニル、ピペラジニル、
(c)0、1、2、若しくは3個のOH、F、-C(=O)OCH3、-NH2、-NH(CH3)、若しくは-N(CH3)2によって置換されるC1-6alkから選択される。
(a)R12はHであるか、
(b)R12は、オキセタニル、シクロプロピルであるか、或いは
(c)R12は、0、1、2、又は3個のOH基によって置換されるC1-6alkである。
R13は、F、Cl、Br、-OH、-OC1-4haloalk、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るC1-6alkである。
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。
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。
スキームAによれば、一実施形態では、本明細書に開示される式(I)の化合物は、以下の通りに合成することができる。
工程1a又は1b:環Ar1化合物の調製:上記のスキームAを参照されたい
工程2b:環Ar2化合物の調製:
スキームCは、本明細書に開示される式(I)の化合物を形成する更に別の代替的方法を提供する。スキームCによれば、工程1aはスキームAに記載される通りに、続いて工程2bはスキームBに記載される通りに、実施することができる。
スキームDは、本明細書に開示される式(I)の化合物を形成する更に別の代替的方法を提供する。スキームDによれば、工程1a又は1bはスキームAに記載される通りに、続いて工程2bはスキームBに記載される通りに、実施することができる。
スキームEは、本明細書に開示される式(I)の化合物を形成する更に別の代替的方法を提供する。スキームEによれば、工程1a又は1bは、スキームAに記載される通りに実施して、化合物A-2を調製することができる。2-フルオロ-4-ニトロ安息香酸、2,5-ジフルオロ-4-ニトロ安息香酸、又は2,6-ジフルオロ-4-ニトロ安息香酸が挙げられるがこれらに限定されない、化合物E-1(式中、W6はハロゲン、例えばフルオロ又はクロロである)は、市販されており、又は当業者により既知の方法に従い合成することもできる。
環AR1中間体:
中間体1:(R)-2-(2-メチルモルホリノ)ピリミジン-4-アミン
中間体12:4-ヨード-2-(6-アザスピロ[2.5]オクタン-6-イル)安息香酸
中間体17:N-(2-クロロ-6-メチルピリミジン-4-イル)-4-ヨード-2-(6-アザスピロ[2.5]オクタン-6-イル)ベンズアミド
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 (43)
- 式(I):
X1はN又は-CR6であり、
R1は-CN、又は基-Z-R12であり、式中、Zは-C0-4アルキレン-、-NR11-、-NR11SO2-、-SO2NR11-、-NR11-S(=O)(=NH)-、-S(=O)(=NH)-、-S-、-S(=O)-、-SO2-、-C0-4アルキレン-O-、-(C=O)-、-(C=O)NR11-、-C=N(OH)-、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の対はこれらのそれぞれに付着した硫黄原子と結合して、0、1、2、又は3個のN原子、並びにO及びSからなる群から選択される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-C0-4アルキレン-、-NH-C0-4アルキレン-、-N(CH3)-C0-4アルキレン-、-C(=O)NRa(C1-4アルキレン)-、-O-C0-4アルキレン-、S、S=O、S(=O)2、-SO2NR13、又は-S(=O)(=NH)-であり、
R3はH、C1-4アルキル、又はC1-4ハロアルキルであり、
R4はH、ハロ、R4a、又はR4bであり、
R5はH、ハロ、C1-8アルキル、又はC1-4ハロアルキルであり、
R6はH、ハロ、C1-8アルキル、C1-4ハロアルキル、-O-C1-8アルキル、又は-O-R6aであり、式中、R6aは、0、1、2、又は3個のN原子、並びにO及びSからなる群から選択される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員単環式環であり、
R7はH、ハロ、C1-8アルキル、又はC1-4ハロアルキルであり、
R8はH、ハロ、C1-8アルキル、C1-4ハロアルキル、-OH、-O-R8a、又は-O-R8bであり、
R9はH、ハロ、C1-8アルキル、又はC1-4ハロアルキルであり、
Rxは、下式:
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付着した炭素原子と結合して、前記Rx環に対する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、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からなる群から選択される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、C1-6アルキル、C1-4ハロアルキル、-ORa、-OC1-4ハロアルキル、CN、-NRaRa、及びオキソからなる群から選択される0、1、2、又は3個の基によって置換され、
R11はH、R11a、又はR11bであり、
R12はH、R12a、又はR12bであり、
R13はR13a又はR13bであり、
R4a、R8a、R10k、R11a、R12a、及びR13aは、独立して、各場合において、F、Cl、Br、C1-6アルキル、C1-4ハロアルキル、-ORa、-OC1-4ハロアルキル、CN、-C(=O)Rb、-C(=O)ORa、-C(=O)NRaRa、-C(=NRa)NRaRa、-OC(=O)Rb、-OC(=O)NRaRa、-OC2-6アルキレンNRaRa、-OC2-6アルキレンORa、-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、-NRaC2-6アルキレンNRaRa、-NRaC2-6アルキレンORa、-C1-6アルキレンNRaRa、-C1-6アルキレンORa、-C1-6アルキレンN(Ra)C(=O)Rb、-C1-6アルキレンOC(=O)Rb、-C1-6アルキレンC(=O)NRaRa、-C1-6アルキレンC(=O)ORa、R14、及びオキソからなる群から選択される0、1、2、又は3個の基によって置換される、0、1、2、又は3個のN原子、並びにO及びSからなる群から選択される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員単環式又は5、6、7、8、9、10、11、若しくは12員二環式環であり、
R4b、R8b、R10l、R11b、R12b、及びR13bは、独立して、各場合において、F、Cl、Br、-ORa、-OC1-4ハロアルキル、及びCNからなる群から選択される0、1、2、3、4、又は5個の基によって置換されるC1-6アルキルからなる群から選択され、
R14は、独立して、各場合において、F、Cl、Br、C1-6アルキル、C1-4ハロアルキル、-ORa、-OC1-4ハロアルキル、CN、-C(=O)Rb、-C(=O)ORa、-C(=O)NRaRa、-C(=NRa)NRaRa、-OC(=O)Rb、-OC(=O)NRaRa、-OC2-6アルキレンNRaRa、-OC2-6アルキレンORa、-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、-NRaC2-6アルキレンNRaRa、-NRaC2-6アルキレンORa、-C1-6アルキレンNRaRa、-C1-6アルキレンORa、-C1-6アルキレンN(Ra)C(=O)Rb、-C1-6アルキレンOC(=O)Rb、-C1-6アルキレンC(=O)NRaRa、-C1-6アルキレンC(=O)ORa、及びオキソからなる群から選択される、0、1、2、又は3個の基によって置換される、0、1、2、又は3個のN原子、並びにO及びSからなる群から選択される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員単環式又は5、6、7、8、9、10、11、若しくは12員二環式環であり、
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、C1-6アルキル、フェニル、又はベンジルであり、前記C1-6アルキルは、ハロ、-OH、-OC1-4アルキル、-NH2、-NHC1-4アルキル、-OC(=O)C1-4アルキル、及び-N(C1-4アルキル)C1-4アルキルからなる群から選択される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、C1-4アルキル、C1-3ハロアルキル、-OH、-OC1-4アルキル、-NH2、-NHC1-4アルキル、-OC(=O)C1-4アルキル、及び-N(C1-4アルキル)C1-4アルキルからなる群から選択される0、1、2、又は3個の置換基によって置換される。 - R3はH又はメチルである、請求項1に記載の化合物、又はその薬学的に許容される塩。
- R10c、R10d、R10e、R10f、R10g、R10h、R10i、及びR10jのそれぞれが、H、ハロ、C1-6アルキル、又はC1-4ハロアルキルであり、R10a及びR10bの対のそれぞれが、これらのそれぞれに付着した炭素原子と結合して、Rx環に対するスピロである飽和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からなる群から選択される0、1、又は2個の原子を含有する、請求項1又は4に記載の化合物、又はその薬学的に許容される塩。
- 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、これらのそれぞれに付着した炭素原子と結合して、Rx環に対する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及び4~5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。
- R1は、-CN、又は基-Z-R12であり、
式中、
Zは、結合、-NH-、-NHSO2-、-SO2NH-、-S(=O)(=NH)-、-S-、-S(=O)-、-SO2-、-(C=O)-、-(C=O)NH-、又は-NH(C=O)-であり、
R12は、
(a)H;
(b)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、オキシラニル、オキセタニル、テトラヒドロフラニル、アゼチジニル、イミダゾリル、モルホリニル、ピロリジニル、ピペラジニル、以下の基:
若しくは、以下の基:
;又は
(c)0、1、2、若しくは3個のOH若しくはFによって置換されるC1-6アルキル
である、請求項1~8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。 - R1は、-CN、又は基-Z-R12であり、
式中、
Zは、結合、-NH-、-NHSO2-、-SO2NH-、-S(=O)(=NH)-、-S-、-S(=O)-、-SO2-、-(C=O)-、-(C=O)NH-、又は-NH(C=O)-であり、
(a)R12はHであるか、
(b)R12は、オキセタニル、シクロプロピルであるか、或いは
(c)R12は、0、1、2、又は3個のOH基によって置換されるC1-6アルキルである、請求項1~9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。 - R1は、基-Z-R12であり、
式中、
Zは、-NHSO2-又は-SO2NH-であり、
R12は、オキセタニル、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るC1-6アルキルである、請求項1~10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。 - R1は、基-Z-R12であり、
式中、
Zは、-NHSO2-であり、
R12は、-CH2-CH2-OHである、請求項1~10又は12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。 - R2は、ハロ又は基-Y-R13であり、
式中、
Yは、結合、-NH-、-NH-(CH2)0-4-、又は-O-(CH2)0-4であり、
R13は、F、Cl、Br、C1-6アルキル、C1-4ハロアルキル、-OH、-OC1-4ハロアルキル、CN、R14、及びオキソからなる群から選択される0、1、2、又は3個の基によって置換される0、1、2、又は3個のN原子、並びにO及びSからなる群から選択される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員単環式又は5、6、7、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ハロアルキル、及びCNからなる群から選択される0、1、2、3、4、又は5個の基によって置換されるC1-6アルキルである、請求項1~13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。 - R2は、飽和5又は6員単環式環であり、各前記環は、0、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、C1-6アルキル、C1-4ハロアルキル、-OH、-OC1-4ハロアルキル、CN、R14、及びオキソからなる群から選択される0、1、2、又は3個の基によって置換される、請求項1~14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。
- R2は、
(a)ハロ;
(b)基-Y-R13であって、
式中、
Yは結合であり、
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、若しくは、下式:
(c)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、下式:
- R2は、F、Cl、Br、メチル、CF3、-OH、-OCHF2、CN、及びオキソからなる群から選択される0、1、2、又は3個の基によって置換されるモルホリニル又はピペリジニルである、請求項1~16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。
- R2は、1、2、又は3個のメチル基によって置換されるモルホリニルである、請求項1~17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。
- R2は、1、2、又は3個のフルオロ基によって置換されるピペリジニルである、請求項1~17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。
- Zは、結合、-NH-、-NHSO2-、-SO2NH-、-S(=O)(=NH)-、-S-、-S(=O)-、-SO2-、-(C=O)-、-(C=O)NH-、又は-NH(C=O)-である、請求項1~10及び12~13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。
- R12は、
(a)H;
(b)F、Cl、Br、-OH、及び-OCH3からなる群から選択される0、1、2、若しくは3個の基によって置換されるC1-6アルキル;又は
(c)F、Cl、Br、C1-6アルキル、C1-4ハロアルキル、-C1-6アルキルOH、-OH、-OCH3、-NH2、 及びオキソからなる群から選択される0、1、2、若しくは3個の基によって置換される、0、1、2、若しくは3個のN原子、並びにO及びSからなる群から選択される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
である、請求項1~8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。 - 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、テトラヒドロフラニル、及び1,3,4-オキサチアジナニルからなる群から選択される、請求項1~8及び22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。
- R4は、
(a)H;
(b)0、1、2、若しくは3個のOH基によって置換されるC1-6アルキル;又は
(c)シクロプロピル
である、請求項1~23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。 - R4はH又はメチルである、請求項1~24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。
- R5はHである、請求項1~25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。
- R6はH又はFである、請求項1又は3~26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。
- R7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、又はその薬学的に許容される塩。
- R8はHである、請求項1~28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。
- R9はHである、請求項1~29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。
- 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、治療的有効量の請求項1~34のいずれか一項に記載の化合物、又はその薬学的に許容される塩を含む、医薬組成物であって、
前記症状が、(a)膀胱、子宮内膜、肺扁平上皮細胞、乳房、結腸、腎臓、肝臓、肺、小細胞肺癌、食道、胆嚢、脳、頭頚部、卵巣、膵臓、胃、子宮頚部、甲状腺、前立腺、及び皮膚のがんからなる群から選択される固形又は血液学的起因の腫瘍、(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、及びバーケットリンパ腫からなる群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なる群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なる群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、及び神経鞘腫からなる群から選択される中枢及び末梢神経系の腫瘍、並びに(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、及びカポジ肉腫からなる群から選択されるがんである、医薬組成物。 - 対象における固形腫瘍の寸法を減少させるための医薬組成物であって、治療的有効量の請求項1~34のいずれか一項に記載の化合物、又はその薬学的に許容される塩を含む、医薬組成物。
- 対象における細胞増殖障害を治療するための医薬組成物であって、治療的有効量の請求項1~34のいずれか一項に記載の化合物、又はその薬学的に許容される塩を含む、医薬組成物。
- 細胞中でKIF18Aを阻害するための医薬組成物であって、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薬剤の調製における、請求項1~34のいずれか一項に記載の化合物、若しくは前記化合物の薬学的に許容される塩、又は請求項35に記載の医薬組成物の使用であって、
前記症状が、(a)膀胱、子宮内膜、肺扁平上皮細胞、乳房、結腸、腎臓、肝臓、肺、小細胞肺癌、食道、胆嚢、脳、頭頚部、卵巣、膵臓、胃、子宮頚部、甲状腺、前立腺、及び皮膚のがんからなる群から選択される固形又は血液学的起因の腫瘍、(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、及びバーケットリンパ腫からなる群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なる群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なる群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、及び神経鞘腫からなる群から選択される中枢及び末梢神経系の腫瘍、並びに(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、及びカポジ肉腫からなる群から選択されるがんである、使用。 - 対象における固形腫瘍の寸法を減少させるための薬剤の調製における、請求項1~34のいずれか一項に記載の化合物、若しくは前記化合物の薬学的に許容される塩、又は請求項35に記載の医薬組成物の使用。
- 対象における細胞増殖障害を治療するための薬剤の調製における、請求項1~34のいずれか一項に記載の化合物、若しくは前記化合物の薬学的に許容される塩、又は請求項35に記載の医薬組成物の使用。
- 細胞中でKIF18Aを阻害するための薬剤の調製における、請求項1~34のいずれか一項に記載の化合物、若しくは前記化合物の薬学的に許容される塩、又は請求項35に記載の医薬組成物の使用。
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