JP2020511454A - Malt1の阻害剤およびそれらの使用 - Google Patents
Malt1の阻害剤およびそれらの使用 Download PDFInfo
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- JP2020511454A JP2020511454A JP2019549411A JP2019549411A JP2020511454A JP 2020511454 A JP2020511454 A JP 2020511454A JP 2019549411 A JP2019549411 A JP 2019549411A JP 2019549411 A JP2019549411 A JP 2019549411A JP 2020511454 A JP2020511454 A JP 2020511454A
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- Prior art keywords
- unsubstituted
- substituted
- pharmaceutically acceptable
- acceptable salt
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960005066 trisodium edetate Drugs 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000875 trofosfamide Drugs 0.000 description 1
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229940094060 tykerb Drugs 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 208000037965 uterine sarcoma Diseases 0.000 description 1
- 229950003520 utomilumab Drugs 0.000 description 1
- 206010046885 vaginal cancer Diseases 0.000 description 1
- 208000013139 vaginal neoplasm Diseases 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229960001722 verapamil 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
- 229960003895 verteporfin Drugs 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine 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-XQKSVPLYSA-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
- 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
- 229960004355 vindesine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound 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 GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical class 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
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 201000005102 vulva cancer Diseases 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical class [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 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
- 229960000641 zorubicin Drugs 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Abstract
Description
本願は、2017年3月8日に出願された米国仮特許出願U.S.S.N. 62/468,758および2017年9月1日に出願された米国仮特許出願U.S.S.N. 62/553,336に対する35 U.S.C.§119(e)下における優先権を主張する。その各々の全体は、本明細書において参照により組み込まれる。
本発明は、一般に、MALT1を阻害を阻害する化合物、および、MALT1関連疾患または障害(例としてがん)の処置における化合物の使用に関する。
びまん性大B細胞リンパ腫(large B-cell lymphoma:DLBCL)は、B細胞のがんであり、成人では最も一般的な型の非ホジキンリンパ腫である。DLBCLは、身体のほとんどいずれの場所においても生じ得る攻撃的な腫瘍である。典型的には、DLBCLは、正常なB細胞から生じるが、また、他の型のリンパ腫または白血病の悪性の形質転換をも表し、根底にある免疫不全が重大なリスクファクターである。処置における進歩にもかかわらず、DLBCL患者のうちの三分の一は、応答しないか、または短時間の内に再発する。DLBCLには、2つの主要な生物学的に区別し得る分子サブタイプ:胚中心B細胞(GCB)および活性化B細胞(ABC)が存在する。ABC−DLBCLは、胚中心B細胞から形質細胞に分化するプロセスにあるB細胞から誘導される。典型的には、ABCのサブタイプを診断された患者は、GCB患者よりも悪い予後を有する。
Aは、
Bは、ピリジニルであり;
R1およびR2の各々の場合は、独立して、ハロゲン、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、置換または非置換のヘテロアルキル、−ORA、−N(RA)2、−SRA、−CN、−SCN、−C(=NRA)RA、−C(=NRA)ORA、−C(=NRA)N(RA)2、−C(=O)RA、−C(=O)ORA、−C(=O)N(RA)2、−S(=O)RA、−S(=O)2RA、−NO2、−NRAC(=O)RA、−NRAC(=O)ORA、−NRAC(=O)N(RA)2、−NRAS(=O)RA、−NRAS(=O)2RA、−S(=O)N(RA)2、−S(=O)2N(RA)2、−OC(=O)RA、−OC(=O)ORA、または−OC(=O)N(RA)2であり;
R3およびR4の各々の場合は、独立して、水素、置換または非置換のアルキル、または窒素保護基であり;
RAの各々の場合は、独立して、水素、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のヘテロアルキル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、窒素原子に結合している場合は窒素保護基、酸素原子に結合している場合は酸素保護基、もしくは硫黄原子に結合している場合は硫黄保護基であるか、または2つのRA基は、連結して、置換または非置換のヘテロ環式環を形成し;
kは、1、2、3、または4であり;および
pは、1、2、3、4、5または6である。
Aは、
Bは、ピリジニルであり;
R1およびR2の各々の場合は、独立して、ハロゲン、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、置換または非置換のヘテロアルキル、−ORA、−N(RA)2、−SRA、−CN、−SCN、−C(=NRA)RA、−C(=NRA)ORA、−C(=NRA)N(RA)2、−C(=O)RA、−C(=O)ORA、−C(=O)N(RA)2、−S(=O)RA、−S(=O)2RA、−NO2、−NRAC(=O)RA、−NRAC(=O)ORA、−NRAC(=O)N(RA)2、−NRAS(=O)RA、−NRAS(=O)2RA、−S(=O)N(RA)2、−S(=O)2N(RA)2、−OC(=O)RA、−OC(=O)ORA、または−OC(=O)N(RA)2であり;
R3およびR4の各々の場合は、独立して、水素、置換または非置換のアルキル、または窒素保護基であり;
RAの各々の場合は、独立して、水素、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のヘテロアルキル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、窒素原子に結合している場合は窒素保護基、酸素原子に結合している場合は酸素保護基、もしくは硫黄原子に結合している場合は硫黄保護基であるか、または2つのRA基は、連結して、置換または非置換のヘテロ環式環を形成し;
kは、1、2、3、または4であり;および
pは、1、2、3、4、5または6である。
具体的な官能基および化学用語の定義がより詳細に下に記載される。化学元素はHandbook of Chemistry and Physics, 75th Ed.内表紙の元素周期表CAS版に従って同定され、具体的な官能基はそこに記載のとおりに一般に定義される。加えて、有機化学の一般の法則、さらには具体的な官能部分および反応性は、Organic Chemistry, Thomas Sorrell, University Science Books, Sausalito, 1999;Smith and March, March's Advanced Organic Chemistry, 5th Edition, John Wiley & Sons, Inc., New York, 2001;Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989;およびCarruthers, Some Modern Methods of Organic Synthesis, 3rd Edition, Cambridge University Press, Cambridge, 1987に記載されている。
または、炭素原子上の2個のジェミナル水素は、基=O、=S、=NN(Rbb)2、=NNRbbC(=O)Raa、=NNRbbC(=O)ORaa、=NNRbbS(=O)2Raa、=NRbb、または=NORccで置き換えられる;
Raaの各々は独立して、C1〜10アルキル、C1〜10ペルハロアルキル、C2〜10アルケニル、C2〜10アルキニル、ヘテロC1〜10アルキル、ヘテロC2〜10アルケニル、ヘテロC2〜10アルキニル、C3〜10カルボシクリル、3〜14員のヘテロシクリル、C6〜14アリール、および5〜14員のヘテロアリールから選択されるか、または2個のRaa基は連結して、3〜14員のヘテロシクリルまたは5〜14員のヘテロアリール環を形成し、ここで各アルキル、アルケニル、アルキニル、ヘテロアルキル、ヘテロアルケニル、ヘテロアルキニル、カルボシクリル、ヘテロシクリル、アリール、およびヘテロアリールは独立して、0、1、2、3、4、または5個のRdd基で置換されている;
Rbbの各々は独立して、水素、−OH、−ORaa、−N(Rcc)2、−CN、−C(=O)Raa、−C(=O)N(Rcc)2、−CO2Raa、−SO2Raa、−C(=NRcc)ORaa、−C(=NRcc)N(Rcc)2、−SO2N(Rcc)2、−SO2Rcc、−SO2ORcc、−SORaa、−C(=S)N(Rcc)2、−C(=O)SRcc、−C(=S)SRcc、−P(=O)(Raa)2、−P(=O)(ORcc)2、−P(=O)(N(Rcc)2)2、C1〜10アルキル、C1〜10ペルハロアルキル、C2〜10アルケニル、C2〜10アルキニル、ヘテロC1〜10アルキル、ヘテロC2〜10アルケニル、ヘテロC2〜10アルキニル、C3〜10カルボシクリル、3〜14員のヘテロシクリル、C6〜14アリール、および5〜14員のヘテロアリールから選択されるか、または2個のRbb基は連結して、3〜14員のヘテロシクリルまたは5〜14員のヘテロアリール環を形成し、ここで各アルキル、アルケニル、アルキニル、ヘテロアルキル、ヘテロアルケニル、ヘテロアルキニル、カルボシクリル、ヘテロシクリル、アリール、およびヘテロアリールは独立して、0、1、2、3、4、または5個のRdd基で置換されている;ここでX−は、対イオンである;
Rccの各々は独立して、水素、C1〜10アルキル、C1〜10ペルハロアルキル、C2〜10アルケニル、C2〜10アルキニル、ヘテロC1〜10アルキル、ヘテロC2〜10アルケニル、ヘテロC2〜10アルキニル、C3〜10カルボシクリル、3〜14員のヘテロシクリル、C6〜14アリール、および5〜14員のヘテロアリールから選択されるか、または2個のRcc基は連結して、3〜14員のヘテロシクリルまたは5〜14員のヘテロアリール環を形成し、ここで各アルキル、アルケニル、アルキニル、ヘテロアルキル、ヘテロアルケニル、ヘテロアルキニル、カルボシクリル、ヘテロシクリル、アリール、およびヘテロアリールは独立して、0、1、2、3、4、または5個のRdd基で置換されている;
Rddの各々は独立して、ハロゲン、−CN、−NO2、−N3、−SO2H、−SO3H、−OH、−ORee、−ON(Rff)2、−N(Rff)2、−N(Rff)3 +X−、−N(ORee)Rff、−SH、−SRee、−SSRee、−C(=O)Ree、−CO2H、−CO2Ree、−OC(=O)Ree、−OCO2Ree、−C(=O)N(Rff)2、−OC(=O)N(Rff)2、−NRffC(=O)Ree、−NRffCO2Ree、−NRffC(=O)N(Rff)2、−C(=NRff)ORee、−OC(=NRff)Ree、−OC(=NRff)ORee、−C(=NRff)N(Rff)2、−OC(=NRff)N(Rff)2、−NRffC(=NRff)N(Rff)2、−NRffSO2Ree、−SO2N(Rff)2、−SO2Ree、−SO2ORee、−OSO2Ree、−S(=O)Ree、−Si(Ree)3、−OSi(Ree)3、−C(=S)N(Rff)2、−C(=O)SRee、−C(=S)SRee、−SC(=S)SRee、−P(=O)(ORee)2、−P(=O)(Ree)2、−OP(=O)(Ree)2、−OP(=O)(ORee)2、C1〜6アルキル、C1〜6ペルハロアルキル、C2〜6アルケニル、C2〜6アルキニル、ヘテロC1〜6アルキル、ヘテロC2〜6アルケニル、ヘテロC2〜6アルキニル、C3〜10カルボシクリル、3〜10員のヘテロシクリル、C6〜10アリール、5〜10員のヘテロアリールから選択されるか(ここで各アルキル、アルケニル、アルキニル、ヘテロアルキル、ヘテロアルケニル、ヘテロアルキニル、カルボシクリル、ヘテロシクリル、アリール、およびヘテロアリールは独立して、0、1、2、3、4、または5個のRgg基で置換されている)、または2個のジェミナルRdd置換基は連結して、=Oまたは=Sを形成し得る;ここでX−は、対イオンである;
Reeの各々は独立して、C1〜6アルキル、C1〜6ペルハロアルキル、C2〜6アルケニル、C2〜6アルキニル、ヘテロC1〜6アルキル、ヘテロC2〜6アルケニル、ヘテロC2〜6アルキニル、C3〜10カルボシクリル、C6〜10アリール、3〜10員のヘテロシクリル、および3〜10員のヘテロアリールから選択され、ここで各アルキル、アルケニル、アルキニル、ヘテロアルキル、ヘテロアルケニル、ヘテロアルキニル、カルボシクリル、ヘテロシクリル、アリール、およびヘテロアリールは独立して、0、1、2、3、4、または5個のRgg基で置換されている;
Rffの各々は独立して、水素、C1〜6アルキル、C1〜6ペルハロアルキル、C2〜6アルケニル、C2〜6アルキニル、ヘテロC1〜6アルキル、ヘテロC2〜6アルケニル、ヘテロC2〜6アルキニル、C3〜10カルボシクリル、3〜10員のヘテロシクリル、C6〜10アリールおよび5〜10員のヘテロアリールから選択されるか、または2個のRff基は連結して、3〜10員のヘテロシクリルまたは5〜10員のヘテロアリール環を形成し、ここで各アルキル、アルケニル、アルキニル、ヘテロアルキル、ヘテロアルケニル、ヘテロアルキニル、カルボシクリル、ヘテロシクリル、アリール、およびヘテロアリールは独立して、0、1、2、3、4、または5個のRgg基で置換されている;および
Rggの各々は独立して、ハロゲン、−CN、−NO2、−N3、−SO2H、−SO3H、−OH、−OC1〜6アルキル、−ON(C1〜6アルキル)2、−N(C1〜6アルキル)2、−N(C1〜6アルキル)3 +X−、−NH(C1〜6アルキル)2 +X−、−NH2(C1〜6アルキル)+X−、−NH3 +X−、−N(OC1〜6アルキル)(C1〜6アルキル)、−N(OH)(C1〜6アルキル)、−NH(OH)、−SH、−SC1〜6アルキル、−SS(C1〜6アルキル)、−C(=O)(C1〜6アルキル)、−CO2H、−CO2(C1〜6アルキル)、−OC(=O)(C1〜6アルキル)、−OCO2(C1〜6アルキル)、−C(=O)NH2、−C(=O)N(C1〜6アルキル)2、−OC(=O)NH(C1〜6アルキル)、−NHC(=O)(C1〜6アルキル)、−N(C1〜6アルキル)C(=O)(C1〜6アルキル)、−NHCO2(C1〜6アルキル)、−NHC(=O)N(C1〜6アルキル)2、−NHC(=O)NH(C1〜6アルキル)、−NHC(=O)NH2、−C(=NH)O(C1〜6アルキル)、−OC(=NH)(C1〜6アルキル)、−OC(=NH)OC1〜6アルキル、−C(=NH)N(C1〜6アルキル)2、−C(=NH)NH(C1〜6アルキル)、−C(=NH)NH2、−OC(=NH)N(C1〜6アルキル)2、−OC(=NH)NH(C1〜6アルキル)、−OC(=NH)NH2、−NHC(=NH)N(C1〜6アルキル)2、−NHC(=NH)NH2、−NHSO2(C1〜6アルキル)、−SO2N(C1〜6アルキル)2、−SO2NH(C1〜6アルキル)、−SO2NH2、−SO2C1〜6アルキル、−SO2OC1〜6アルキル、−OSO2C1〜6アルキル、−SOC1〜6アルキル、−Si(C1〜6アルキル)3、−OSi(C1〜6アルキル)3、−C(=S)N(C1〜6アルキル)2、C(=S)NH(C1〜6アルキル)、C(=S)NH2、−C(=O)S(C1〜6アルキル)、−C(=S)SC1〜6アルキル、−SC(=S)SC1〜6アルキル、−P(=O)(OC1〜6アルキル)2、−P(=O)(C1〜6アルキル)2、−OP(=O)(C1〜6アルキル)2、−OP(=O)(OC1〜6アルキル)2、C1〜6アルキル、C1〜6ペルハロアルキル、C2〜6アルケニル、C2〜6アルキニル、ヘテロC1〜6アルキル、ヘテロC2〜6アルケニル、ヘテロC2〜6アルキニル、C3〜10カルボシクリル、C6〜10アリール、3〜10員ヘテロシクリル、5〜10員ヘテロアリールである;または、2つのジェミナルRgg置換基は連結して、=Oまたは=Sを形成し得る;ここでX−は、対イオンである。
以下の定義は、本願全体にわたり用いられる、より一般的な用語である。
本明細書において提供されるのは、MALT1の阻害剤である。一側面において、本開示は、式Iの化合物、およびその薬学的に受入可能な塩、溶媒和物、水和物、多型、共結晶、互変異生体、立体異性体、放射性標識された誘導体、プロドラッグ、および医薬組成物を提供する。化合物は、それを必要とする対象におけるMALT1活性に関連する疾患(例として、自己免疫性疾患、炎症性疾患、増殖性疾患、がん(例としてDLBCL))の処置および/または予防のために有用である。
本明細書において記載される化合物は、MALT1と相互作用する。本明細書において記載されるように、治療効果は、本明細書において記載される化合物による、MALT1の阻害、分解、調節、結合、および/または修飾の結果であってもよい。ある態様において、化合物は、MALT1のアロステリック部位に結合することによって、MALT1を阻害、分解、調節、および/または修飾する。化合物は、本明細書において記載される任意の組成物、キット、または方法における使用のために、その薬学的に受入可能な塩、共結晶、互変異生体、立体異性体、溶媒和物、水和物、多型、同位体が濃縮された誘導体、またはプロドラッグとして、提供されてもよい。
Aは、
Bは、ピリジニルであり;
R1およびR2の各々の場合は、独立して、ハロゲン、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、置換または非置換のヘテロアルキル、−ORA、−N(RA)2、−SRA、−CN、−SCN、−C(=NRA)RA、−C(=NRA)ORA、−C(=NRA)N(RA)2、−C(=O)RA、−C(=O)ORA、−C(=O)N(RA)2、−S(=O)RA、−S(=O)2RA、−NO2、−NRAC(=O)RA、−NRAC(=O)ORA、−NRAC(=O)N(RA)2、−NRAS(=O)RA、−NRAS(=O)2RA、−S(=O)N(RA)2、−S(=O)2N(RA)2、−OC(=O)RA、−OC(=O)ORA、または−OC(=O)N(RA)2であり;
R3およびR4の各々の場合は、独立して、水素、置換または非置換のアルキル、または窒素保護基であり;
RAの各々の場合は、独立して、水素、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のヘテロアルキル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、窒素原子に結合している場合は窒素保護基、酸素原子に結合している場合は酸素保護基、または硫黄原子に結合している場合は硫黄保護基、または2つのRA基は、連結して、置換または非置換のヘテロ環式環を形成し;
kは、1、2、3、4、5、または6であり;および
pは、1、2、3、または4である。
Aは、
Bは、ピリジニルであり;
R1およびR2の各々の場合は、独立して、ハロゲン、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、置換または非置換のヘテロアルキル、−ORA、−N(RA)2、−SRA、−CN、−SCN、−C(=NRA)RA、−C(=NRA)ORA、−C(=NRA)N(RA)2、−C(=O)RA、−C(=O)ORA、−C(=O)N(RA)2、−S(=O)RA、−S(=O)2RA、−NO2、−NRAC(=O)RA、−NRAC(=O)ORA、−NRAC(=O)N(RA)2、−NRAS(=O)RA、−NRAS(=O)2RA、−S(=O)N(RA)2、−S(=O)2N(RA)2、−OC(=O)RA、−OC(=O)ORA、または−OC(=O)N(RA)2であり;
R3およびR4の各々の場合は、独立して、水素、置換または非置換のアルキル、または窒素保護基であり;
RAの各々の場合は、独立して、水素、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のヘテロアルキル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、窒素原子に結合している場合は窒素保護基、酸素原子に結合している場合は酸素保護基、または硫黄原子に結合している場合は硫黄保護基、または2つのRA基は、連結して、置換または非置換のヘテロ環式環を形成し;
kは、1、2、3、4、5、または6であり;および
pは、1、2、3、または4である。
ある態様において、RAは、独立して、水素、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のヘテロアルキル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、窒素原子に結合している場合は窒素保護基、酸素原子に結合している場合は酸素保護基、または硫黄原子に結合している場合は硫黄保護基であるか、あるいは、2つのRA基は、連結して、置換または非置換のヘテロ環式環を形成する。ある態様において、RAは、独立して、水素、置換または非置換のアルキル、置換または非置換のヘテロアルキル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、窒素原子に結合している場合は窒素保護基、酸素原子に結合している場合は酸素保護基であるか、あるいは、2つのRA基は、連結して、置換または非置換のヘテロ環式環を形成する。
本開示は、式Iの化合物、またはその薬学的に受入可能な塩、共結晶、互変異生体、立体異性体、溶媒和物、水和物、多型、同位体が濃縮された誘導体、またはプロドラッグ、および任意に薬学的に受入可能な賦形剤を含む医薬組成物を提供する。ある態様において、本明細書において記載される医薬組成物は、式Iの化合物、またはその薬学的に受入可能な塩、および薬学的に受入可能な賦形剤を含む。
CBM複合体内で足場タンパク質として作用することに加えて、MALT1はまた、ABC−DLBCLなどのあるがんにおいて構成的に活性化されるタンパク質の分解活性を有する。MALT1阻害剤は、ABC−DLBCLのバイアビリティーを阻害することが知られており、これが、MALT1の阻害を、ABC−DLBCLの処置のための魅力的な方法にしている。加えて、一部のABC−DLBCL細胞は、CARD11活性化突然変異を持つ。これらの突然変異を伴った細胞は、MALT1阻害剤に対してとりわけ感受性であり、一方、それらは、経路における上流のキナーゼ(例としてBTK)の阻害剤に対して抵抗性である。したがって、MALT1阻害剤によるこれらのがんの処置は、とりわけ有効であり得る。
本明細書に記載の発明がより完全に理解され得るために、以下の例を記す。本出願に記載の例は、本明細書に提供される化合物、医薬組成物および方法を説明するために提示されるが、これらの範囲を限定するものとして、決して解釈されるべきではない。
合成中間体の調製
4−ブロモ−6−クロロキノリン−3−アミン(E)
4−イソプロピルキノリン−3−アミン(U)
4−シクロペンチルキノリン−3−アミン(W)
4−メチルキノリン−3−カルボン酸(KK)
4−シクロプロピル−7−フルオロキノリン−3−カルボン酸(OO)
4−アセチルキノリン−3−カルボン酸(RR)
4−(1−メトキシエチル)キノリン−3−カルボン酸(WW)
4−(1−アジドエチル)キノリン−3−カルボン酸(YY)
6−フルオロ−4−(1−メトキシエチル)キノリン−3−アミン(BBB)
3−クロロ−5−イソシアナート−2−(2H−1,2,3−トリアゾール−2−イル)ピリジン(III):
5−クロロ−6−(トリアゾール−2−イル)ピリジン−3−アミン(NNN)
(7−シクロプロピル−2−メチルチアゾロ[5,4−b]ピリジン−6−イル)カルバミン酸tert−ブチル(TTT)
7−(1−エトキシエチル)−2−メチルチアゾロ[5,4−b]ピリジン−6−カルボン酸(WWW)
1−(6−クロロ−4−(2−メトキシプロパン−2−イル)キノリン−3−イル)−3−(5−クロロ−6−(2H−1,2,3−トリアゾール−2−イル)ピリジン−3−イル)尿素(1)
1−(6−ブロモ−4−メチルキノリン−3−イル)−3−(5−クロロ−6−(2H−1,2,3−トリアゾール−2−イル)ピリジン−3−イル)尿素(25)
1−(5−クロロ−6−(2H−1,2,3−トリアゾール−2−イル)ピリジン−3−イル)−3−(4−(1−ヒドロキシエチル)キノリン−3−イル)尿素(32)
1−(7−シクロプロピル−2−メチルチアゾロ[5,4−b]ピリジン−6−イル)−3−(2−(トリフルオロメチル)ピリジン−4−イル)尿素(33)
表1は、例示化合物についてのMALT1阻害データ(IC50)および細胞増殖阻害データ(GI50)を示す細胞アッセイデータの結果を提供する。MALT1阻害レポーターシステムの使用によってMALT1阻害を実証し、OCI−LY3リンパ腫細胞株の使用によって細胞増殖阻害を実証した。結果は、本開示の化合物が細胞内における強力なMALT1阻害剤であり、および、MALT1の阻害が、がん細胞の有意な成長阻害をもたらすことを示す。
レポーターシステムは、蛍ルシフェラーゼ酵素がc−AMP結合タンパク質部分によって2つの成分に分離された、分割ルシフェラーゼ技術(Promega GloSensorTM)を利用した。cAMPの結合は、光のアウトプットの引き金になる立体構造変化を誘導する。RelB切断部位に基づくMALT1切断シグナルは、cAMP結合のために必要な立体構造変化が、MALT1に媒介される切断後にのみ起こるように、加工された。MALT1切断から独立したルシフェラーゼ活性の干渉のためのコントロールに、Renillaルシフェラーゼを使用した。B細胞受容体シグナリングがホルボール12−ミリスタート13−アセタート(PMA)とイオノマイシンとで活性化されてMALT1プロテアーゼ活性の引き金となる、安定なRajiレポーター細胞株を生成した。Raji MALT1レポーター細胞に、前処置を30分間阻害剤で、および次にPMA/イオノマイシンで1時間行い、および、化合物を評定するためにIC50を使用した。
化合物を5μLでプレーティングし、次に、2,000細胞/ウェルを、45μLで、384−ウェル白色/透明プレート(BD 353963)の中にプレーティングした。細胞を、37℃で96時間増殖させた。
1. 細胞を、アッセイ中に十分な数が存在していることを確認するために数えた。細胞を遠心分離し(300×g 5分)および4.44x104細胞/mLで新鮮な媒体に再懸濁させた。
2. 化合物の希釈物を調製した:希釈標準溶液(working dilutions)は、試験した最高濃度の10×であり、および連続希釈のために96−ウェルV底プレート中で調製した。各アッセイにおいて試験した全ての化合物は、DMSOの、ならびに連続希釈物の、同じ濃度を有した。
3. 化合物のプレーティングをトリプリケートで行った:5μL/ウェル。(標準曲線のための対照の12ウェル(3つのブランク、9つの標準および陽性対照としての50μMのz-VRPR-fmkの3つのウェル)を包含した)。
4. 細胞を、45μL/ウェルの濃度でプレーティングした。ブランクとしては、細胞の代わりに、添加した45μLの媒体とともに3つの対照ウェルを利用した(5μLのビヒクル)。
5. プレートを、確実に泡がなくなるように軽くスピンダウンした。プレートを、次に、37℃で48時間インキュベートし、次にステップ2〜5を繰り返した。
6. 対照細胞の対数増殖を、ビヒクルで処置した細胞のトリパンブルー計数によって評価した。
7. 50μLのCTGlo(Promega)を添加し、2分間揺動させることがこれに続き、次に、10分間室温でインキュベートした。発光を測定した。
クレームにおいて、「a」、「an」、および「the」などの冠詞は、1または1より多いことを意味してもよいが、それと反する指示がないか、またはそれとは別に、文脈から明らかでない場合に限る。ある群の1以上のメンバー間に「または」を包含するクレームまたは記載は、その群のメンバーのうち、1つ、1つより多いか、または、すべてが、所定の生成物またはプロセスに存在するか、それに採用されるか、またはそれとは別に、それに関係があるか、を満たすと考えるが、それと反する指示がないか、またはそれとは別に、文脈から明らかでない場合に限る。本発明は、その群のうち、正確に1つのメンバーが、所定の生成物またはプロセスに存在するか、それに採用されるか、またはそれとは別に、それに関係がある態様を包含する。本発明は、その群のメンバーのうち、1つより多いかまたはすべてが、所定の生成物またはプロセスに存在するか、それに採用されるか、またはそれとは別に、それに関係がある態様を包含する。
Claims (78)
- 式I:
Aは、
Bは、ピリジニルであり;
R1およびR2の各々の場合は、独立して、ハロゲン、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、置換または非置換のヘテロアルキル、−ORA、−N(RA)2、−SRA、−CN、−SCN、−C(=NRA)RA、−C(=NRA)ORA、−C(=NRA)N(RA)2、−C(=O)RA、−C(=O)ORA、−C(=O)N(RA)2、−S(=O)RA、−S(=O)2RA、−NO2、−NRAC(=O)RA、−NRAC(=O)ORA、−NRAC(=O)N(RA)2、−NRAS(=O)RA、−NRAS(=O)2RA、−S(=O)N(RA)2、−S(=O)2N(RA)2、−OC(=O)RA、−OC(=O)ORA、または−OC(=O)N(RA)2であり;
R3およびR4の各々の場合は、独立して、水素、置換または非置換のアルキル、または窒素保護基であり;
RAの各々の場合は、独立して、水素、置換または非置換のアシル、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のヘテロアルキル、置換または非置換のカルボシクリル、置換または非置換のヘテロシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、窒素原子に結合している場合は窒素保護基、酸素原子に結合している場合は酸素保護基、もしくは硫黄原子に結合している場合は硫黄保護基であるか、または2つのRA基は、連結して、置換または非置換のヘテロ環式環を形成し;
kは、1、2、3、または4であり;および
pは、1、2、3、または4である、
の化合物、またはその薬学的に受入可能な塩。 - Aが、
請求項1に記載の化合物、またはその薬学的に受入可能な塩。 - Aが、
請求項1に記載の化合物、またはその薬学的に受入可能な塩。 - Aが、
請求項1に記載の化合物、またはその薬学的に受入可能な塩。 - Aが、
請求項1に記載の化合物、またはその薬学的に受入可能な塩。 - Bが、
請求項1〜5のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。 - Bが、
請求項1〜6のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。 - Bが、
請求項1〜7のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。 - Bが、
請求項1〜5のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。 - Bが、
請求項1〜6および9のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。 - R1の各々の場合が、独立して、ハロゲン、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のヘテロシクリル、置換または非置換のカルボシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、置換または非置換のヘテロアルキル、または−ORAである、請求項1〜10のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、独立して、ハロゲン、置換または非置換のアルキル、置換または非置換のカルボシクリル、置換または非置換のヘテロアリール、置換または非置換のヘテロアルキル、または−ORAである、請求項1〜10のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、独立して、ハロゲン、非置換のC1〜6アルキル、C1〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、C1〜6アジドアルキル、C1〜6ハロアルキル、非置換の5または6員の単環式ヘテロアリール、非置換のC3〜6シクロアルキル、または−OC1〜6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、またはその薬学的に受入可能な塩。
- R1の各々の場合が、ハロゲン、非置換のC1〜6アルキル、C2〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、または非置換のC3〜4シクロアルキルである、請求項1〜10のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R2の各々の場合が、独立して、ハロゲン、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のアルキニル、置換または非置換のヘテロシクリル、置換または非置換のカルボシクリル、置換または非置換のアリール、置換または非置換のヘテロアリール、置換または非置換のヘテロアルキル、または−ORAである、請求項1〜14のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R2の各々の場合が、独立して、ハロゲン、置換または非置換のアルキル、または置換または非置換のヘテロアリールである、請求項1〜14のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R2の各々の場合が、独立して、ハロゲン、C1〜6ハロアルキル、または非置換の5員の単環式ヘテロアリールである、請求項1〜14のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R3が、水素である、請求項1〜17のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R4が、水素である、請求項1〜18のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- kが、1または2である、請求項1〜19のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- pが、1または2である、請求項1〜20のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- 式I−c:
- 式I−d:
- 式I−e:
- R1が、ハロゲン、非置換のC1〜6アルキル、C1〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、C1〜6アジドアルキル、C1〜6ハロアルキル、または非置換のC3〜4シクロアルキルである、請求項1〜10および15〜24のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R2の各々の場合が、独立して、ハロゲン、あるいは環中に2または3個の窒素原子を有する非置換の5員の単環式ヘテロアリール環である、請求項1〜14および18〜24のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1が、ハロゲン、非置換のC1〜6アルキル、C1〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、C1〜6アジドアルキル、C1〜6ハロアルキル、または非置換のC3〜4シクロアルキルであり;およびR2の各々の場合が、独立して、ハロゲン、あるいは環中に2または3個の窒素原子を有する非置換の5員の単環式ヘテロアリール環である、請求項1〜10および18〜24のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- 式I−f:
- R1の各々の場合は、独立して、ハロゲン、非置換のC3〜4シクロアルキル、または−OC1〜6アルキルである、請求項1〜10、15〜24および28のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、独立して、ハロゲン、非置換のC1〜6アルキル、C2〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、または非置換のC3〜4シクロアルキルである、請求項1〜10、15〜24および28のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R2の各々の場合が、独立して、ハロゲン、あるいは環中に2または3個の窒素原子を有する非置換の5員の単環式ヘテロアリール環である、請求項1〜10、18〜24および28〜30のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、独立して、ハロゲン、非置換のC3〜4シクロアルキル、または−OC1〜6アルキルであり;およびR2の各々の場合が、独立して、ハロゲン、あるいは環中に2または3個の窒素原子を有する非置換の5員の単環式ヘテロアリール環である、請求項1〜10、18〜24および28のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、ハロゲン、非置換のC1〜6アルキル、C2〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、または非置換のC3〜4シクロアルキルであり;およびR2の各々の場合が、独立して、ハロゲン、あるいは環中に2または3個の窒素原子を有する非置換の5員の単環式ヘテロアリール環である、請求項1〜10、18〜24および28のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- 式I−g:
- R1が、ハロゲン、非置換のC1〜6アルキル、C1〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、C1〜6アジドアルキル、C1〜6ハロアルキル、または非置換のC3〜4シクロアルキルである、請求項1〜10、15〜24、28および34のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1が、−Br、−CH3、−CH(CH3)2、−C(CH3)2OCH3、−CH(OCH3)CH3、−CH(OH)CH3、−CH(N3)CH3、CF3、または非置換のシクロプロピルである、請求項1〜10、15〜24、28および34のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R2が、ハロゲンである、請求項1〜10、18〜24、28および34〜36のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R2が、−Clである、請求項1〜10、18〜24、28および34〜36のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1が、ハロゲン、非置換のC1〜6アルキル、C1〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、C1〜6アジドアルキル、C1〜6ハロアルキル、または非置換のC3〜4シクロアルキルであり;およびR2が、ハロゲンである、請求項1〜10、18〜24、28および34のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- 式I−h:
- R1の各々の場合が、独立して、ハロゲン、非置換のC3〜4シクロアルキル、または−OC1〜6アルキルである、請求項1〜10、15〜24、28、34および40のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、独立して、−Cl、−Br、−F、非置換のシクロプロピル、または−OCH3である、請求項1〜10、15〜24、28、34および40のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、ハロゲン、非置換のC1〜6アルキル、C2〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、または非置換のC3〜4シクロアルキルである、請求項1〜10、15〜24、28、34および40のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、−F、メチル、−C(CH3)2OCH3、−CH(OCH3)CH3、−CH(OH)CH3、−CH(OCH2CH3)CH3、または非置換のシクロプロピルである、請求項1〜10、15〜24、28、34および40のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R2が、ハロゲンである、請求項40〜44のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R2が、−Clである、請求項40〜44のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、独立して、ハロゲン、非置換のC3〜4シクロアルキル、または−OC1〜6アルキルであり;および各々のR2が、ハロゲンである、請求項1〜10、18〜24、28、34および40のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
- R1の各々の場合が、ハロゲン、非置換のC1〜6アルキル、C2〜6アルコキシアルキル、C1〜6ヒドロキシアルキル、または非置換のC3〜4シクロアルキルであり;および各々のR2が、ハロゲンである、請求項1〜10、18〜24、28、34および40のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩。
-
-
である、請求項1に記載の化合物、またはその薬学的に受入可能な塩。 - 式
- 請求項1〜51のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩、および薬学的に受入可能な賦形剤を含む、医薬組成物。
- MALT1の活性を阻害する方法であって、請求項1〜51のいずれか一項に記載の化合物をMALT1と接触させることを含む、前記方法。
- MALT1が、細胞中にある、請求項53に記載の方法。
- MALT1が、ヒト細胞中にある、請求項53に記載の方法。
- MALT1が、対象中にある、請求項53に記載の方法。
- それを必要とする対象において増殖性疾患、自己免疫性疾患、または炎症性疾患を処置する方法であって、請求項1〜51のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩、または請求項52に記載の医薬組成物を、対象に投与することを含む、前記方法。
- それを必要とする対象においてがんを処置する方法であって、請求項1〜51のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩、または請求項52に記載の医薬組成物を、対象に投与することを含む、前記方法。
- がんが、血液がんである、請求項58に記載の方法。
- がんが、リンパ性腫瘍である、請求項58に記載の方法。
- がんが、白血病、リンパ腫、または多発性骨髄腫である、請求項58に記載の方法。
- がんが、びまん性大B細胞リンパ腫(DLBCL)である、請求項58〜61のいずれか一項に記載の方法。
- がんが、活性化B細胞様びまん性大B細胞リンパ腫(ABC−DLBCL)である、請求項58〜61のいずれか一項に記載の方法。
- それを必要とする対象における増殖性疾患、自己免疫性疾患、または炎症性疾患の処置における使用のための、請求項1〜51のいずれか一項に記載の化合物。
- それを必要とする対象におけるがんの処置における使用のための、請求項1〜51のいずれか一項に記載の化合物。
- がんが、血液がんである、請求項65に記載の化合物。
- がんが、リンパ性腫瘍である、請求項65に記載の化合物。
- 血液がんが、白血病、リンパ腫、または多発性骨髄腫である、請求項66に記載の化合物。
- がんが、びまん性大B細胞リンパ腫(DLBCL)である、請求項65〜68のいずれか一項に記載の化合物。
- がんが、活性化B細胞様びまん性大B細胞リンパ腫(ABC−DLBCL)である、請求項65〜68のいずれか一項に記載の化合物。
- それを必要とする対象における増殖性疾患、自己免疫性疾患、または炎症性疾患の処置における使用のための、請求項52に記載の医薬組成物。
- それを必要とする対象におけるがんの処置における使用のための、請求項52に記載の医薬組成物。
- がんが、血液がんである、請求項72に記載の医薬組成物。
- がんが、リンパ性腫瘍である、請求項72に記載の医薬組成物。
- 血液がんが、白血病、リンパ腫、または多発性骨髄腫である、請求項73に記載の医薬組成物。
- がんが、びまん性大B細胞リンパ腫(DLBCL)である、請求項72〜75のいずれか一項に記載の医薬組成物。
- がんが、活性化B細胞様びまん性大B細胞リンパ腫(ABC−DLBCL)である、請求項72〜75のいずれか一項に記載の医薬組成物。
- 請求項1〜51のいずれか一項に記載の化合物、またはその薬学的に受入可能な塩、または請求項52に記載の医薬組成物;および
前記化合物、その薬学的に受入可能な塩、または医薬組成物を対象に投与するための説明書
を含む、キット。
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US62/553,336 | 2017-09-01 | ||
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US20190275012A9 (en) * | 2016-07-29 | 2019-09-12 | Lupin Limited | Substituted thiazolo-pyridine compounds as malt1 inhibitors |
IL260956B (en) | 2018-08-02 | 2022-01-01 | Applied Materials Israel Ltd | Electron detection sensor |
MX2021005877A (es) * | 2018-11-28 | 2021-07-16 | Takeda Pharmaceuticals Co | Compuesto heterociclico. |
WO2020185926A1 (en) * | 2019-03-12 | 2020-09-17 | Quidel Corporation | Compositions, kits, and methods for detecting autoantibodies |
WO2020208222A1 (en) * | 2019-04-11 | 2020-10-15 | Janssen Pharmaceutica Nv | Pyridine rings containing derivatives as malt1 inhibitors |
WO2021000855A1 (en) * | 2019-07-01 | 2021-01-07 | Qilu Regor Therapeutics Inc. | Malt1 inhibitors and uses thereof |
US20230192685A1 (en) * | 2020-05-27 | 2023-06-22 | Takeda Pharmaceutical Company Limited | Method for producing heterocyclic compound |
US20230414629A1 (en) * | 2020-11-12 | 2023-12-28 | Monopteros Therapeutics, Inc. | Materials and methods of treating cancer |
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US11248007B2 (en) | 2022-02-15 |
JP7142022B2 (ja) | 2022-09-26 |
US20200385405A1 (en) | 2020-12-10 |
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