WO2011056744A1 - IRE-1 α INHIBITORS - Google Patents
IRE-1 α INHIBITORS Download PDFInfo
- Publication number
- WO2011056744A1 WO2011056744A1 PCT/US2010/054940 US2010054940W WO2011056744A1 WO 2011056744 A1 WO2011056744 A1 WO 2011056744A1 US 2010054940 W US2010054940 W US 2010054940W WO 2011056744 A1 WO2011056744 A1 WO 2011056744A1
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- WIPO (PCT)
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- alkoxylalkyl
- halogen
- Prior art date
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- 0 C*C1CC(**)CC1 Chemical compound C*C1CC(**)CC1 0.000 description 9
- FPSSCTNHFNKCSO-UHFFFAOYSA-N OC(COc1cc2c(C=O)c(O)ccc2cc1)=O Chemical compound OC(COc1cc2c(C=O)c(O)ccc2cc1)=O FPSSCTNHFNKCSO-UHFFFAOYSA-N 0.000 description 1
- HRGVUPAZEIIYIV-UHFFFAOYSA-N Oc1ccc(ccc(OCC(N2CCOCC2)=O)c2)c2c1C=O Chemical compound Oc1ccc(ccc(OCC(N2CCOCC2)=O)c2)c2c1C=O HRGVUPAZEIIYIV-UHFFFAOYSA-N 0.000 description 1
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- IRE-la inhibitor compounds of the invention can meet either or both of the following criteria: a. Some compounds of the invention inhibit IRE-la in the in vitro assay with an IC50 of approximately 0.0005-20 ⁇ . Some of these compounds have an IC50 in this assay of approximately 1-20 ⁇ . Others have an IC 50 in this assay of approximately 0.1-1 ⁇ . Still others have an IC 50 of approximately 0.0005-0.1 ⁇ . b. Some compounds of the invention inhibit IRE-la in an in vivo XBP-1 splicing assay ⁇ e.g., in myeloma cells) with an EC 50 in the range of approximately 0.05-80 ⁇ . Some of these compounds have an ECO 50 in this assay of approximately 10- 80 ⁇ . Others have an ECO 50 in this assay of approximately 1-10 ⁇ . Still others have an ECO 50 in this assay of approximately 0.05-1 ⁇ .
- hydroxylalkyl as used herein means an alkyl group as defined above which is substituted with a hydroxy 1 group.
- perfiuoroalkoxyl— CN — CONH 2 ,— CON(CH 3 ) 2 , alkyl, alkoxy, hydroxylalkyl, and alkoxylalkyl; a 5- or 6-membered heterocycle, optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of halogen, — CN,— CONH 2 ,— CON(CH 3 ) 2 , perfluoroalkyl, perfluoroalkoxy, alkyl, alkoxy, hydroxylalkyl, and alkoxylalkyl; or a 5- or 6-membered heteroaryl, optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of halogen, perfluoroalkyl, perfluoroalkyoxyl,— CN,— CONH 2i — CON(CH 3 ) 2 , alkyl, alkoxy, hydroxylalkyl, and alkoxylalkyl;
- Another embodiment includes only those compounds of formula (Id) in which R5, R6, and R7 independently are y u - R9
- Another embodiment includes only those compounds of formula (Id) in which R5, R6,
- Another embodiment includes only those compounds of formula (Id) in which one or more of the alkyls, alkoxys, hydroxylalkyls, or alkoxylalkyls independently are C1-C4 alkyl, C2-C6 or C2-C4 alkoxy, C1-C4 hydroxylalkyl, or C1-C4 alkoxylalkyl.
- R9 and RIO together with the atoms to which they are attached, form a 4-, 5-, 6-, or 7- membered heteroaryl or heterocycle containing 1 or 2 heteroatoms selected from N, O and S, optionall substituted with alkyl; or
- the alkyl is C1-C4 alkyl.
- R3 is hydrogen.
- Another embodiment includes only those compounds of formula (2b) in which Het is linked via a carbon atom.
- Another embodiment includes only those compounds of formula (2c) in which R3
- n 0, 1 , 2, or 3; and R12 is alkoxy or a 5- or 6- membered saturated heterocycle having one or two heteroatoms selected from O, N, and S and optionally substituted with alkyl;
- Some embodiments of the invention include only compounds which have structural formula (4):
- non-toxic salts include those derived from inorganic acids such as hydrochloric, hydrobromic, sulfuric, sulfamic, phosphoric, nitric and the like, as well as salts prepared from organic acids such as acetic, propionic, succinic, glycolic, stearic, lactic, malic, tartaric, citric, ascorbic, pamoic, maleic, hydroxymaleic, phenylacetic, glutamic, benzoic, salicylic, sulfanilic, 2-acetoxy- benzoic, fumaric, toluenesulfonic, benzenesulfonic, methanesulfonic, ethane disulfonic, oxalic, isethionic, trifluoroacetic and the like.
- inorganic acids such as hydrochloric, hydrobromic, sulfuric, sulfamic, phosphoric, nitric and the like
- organic acids such as acetic, propionic,
- compositions of the invention can be manufactured by methods well known in the art, including conventional mixing, dissolving, granulating, dragee-making, levigating, emulsifying, encapsulating, entrapping, or lyophilizing processes.
- compositions of the invention can be delivered in the form of an aerosol sprays from a pressurized pack or a nebulizer, with the use of a suitable propellant, e.g., dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane, carbon dioxide, or other suitable gas.
- a valve can be used to deliver a metered amount.
- Capsules and cartridges of, e.g., gelatin for use in an inhaler or insufflator can be formulated containing a powder mix of an IRE- la inhibitor compound or prodrug thereof and a suitable powder base, such as lactose or starch.
- compositions such as suppositories or retention enemas, e.g., containing conventional suppository bases such as cocoa butter or other glycerides.
- IRE-la inhibitor compounds or prodrugs thereof can be administered to a patient
- disorders associated with the UPR means conditions for which pathogenesis can be advantageously impacted by inhibition of the UPR. In various embodiments of the invention such inhibition of the UPR is
- cytoprotective arm of the unfolded protein response plays an anti-apototic role in tumor survival.
- bio- and chemotherapeutic drugs and radiation treatments may further impact the protein folding and degradation cycle in the ER thereby inducing the UPR as a protective resistance mechanism.
- Patients succumb to cancer because either the tumor is resistant to conventional therapies or returns in a resistant form after an initial response to treatment and, therefore, new treatments and treatment combinations are needed.
- Proteasome inhibitors and Hsp90 inhibitors are thought to act in part by blocking protein degradation and folding, respectively, inducing apoptosis (Davenport et al., Blood 2007 Oct 1;110(7):2641-9). Although it is clear that Hsp90 inhibitors induce XBP-1 splicing and activation of the UPR, it is less clear that proteasome inhibitors activate IRE- la. Current scientific literature suggest that IRE- la is not or is only minimally activated by proteasome inhibitors, such as bortezomib or MG-132 (Davenport et al., Blood 2007 Oct l;110(7):2641-9).
- Interference with UPR may sensitize cancer cells to various chemotherapeutics that elevate the cellular stress.
- Combination therapies which include IRE- la inhibitors may become important therapies in conjunction with current and future standard of care in cancer.
- Cancer therapeutic agents which can be used according to the invention include, but are not limited to, agents in the following categories (which may overlap): a. proteasome inhibitors, such as bortezomib ([(lR)-3-methyl-l-[[(2S)-l-oxo-3- phenyl-2-[(pyrazinylcarbonyl) amino]propyl]amino]butyl] boronic acid; MG-341 ; VELCADE®), MG-132 (N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(l S)-l- formyl-3-methylbutyl]-L-leucinamide); b. antimetabolites, such as: i. pyrimidine analogs (e.g., 5-fluorouracil, floxuridine, capecitabine,
- cyclophosphamide and analogs melphalan, chlorambucil), ethylenimines and methylmelamines (e.g., hexamethylmelamine and thiotepa), alkyl sulfonates-busulfan, nitrosoureas (e.g., carmustine (BCNU) and analogs, streptozocin), trazenes - dacarbazinine (DTIC); d. microtubule disruptors such as taxane (paclitaxel, docetaxel), vincristin,
- doxorubicin doxorubicin, epirubicin, hexamethylmelamineoxaliplatin, iphosphamide, melphalan, merchlorethamine, mitomycin, mitoxantrone, nitrosourea, paclitaxel, plicamycin, procarbazine, teniposide, triethylenethiophosphoramide and etoposide (VP 16); f. antibiotics, such as dactinomycin (actinomycin D), daunorubicin, doxorubicin (adriamycin), idarubicin, anthracyclines, mitoxantrone, bleomycins, plicamycin (mithramycin) and mitomycin; g.
- urokinase aspirin
- COX-2 inhibitors dipyridamole, ticlopidine, clopidogrel, abciximab
- n antimigratory agents
- o antisecretory agents
- immunosuppressives e.g., cyclosporine, tacrolimus (FK-506), sirolimus (rapamycin), azathioprine, mycophenolate mofetil
- p. anti-angiogenic compounds e.g., TNP -470, genistein
- the cancer therapeutic agent is selected from the group consisting of alemtuzumab, aminoglutethimide, amsacrine, anastrozole, asparaginase, beg, bevacizumab, bicalutamide, bleomycin, bortezomib, buserelin, busulfan, campothecin, capecitabine, carboplatin, carmustine, CeaVac, cetuximab, chlorambucil, cisplatin, cladribine, clodronate, colchicine, cyclophosphamide, cyproterone, cytarabine, dacarbazine, daclizumab, dactinomycin, daunorubicin, dienestrol, diethylstilbestrol, docetaxel, doxorubicin, edrecolomab, epirubicin, epratuzumab, erlotinib, estradiol,
- LD 50 the dose lethal to 50% of the population
- ED 50 the dose therapeutically effective in 50% of the population
- the dosage may vary depending upon the dosage form and route of administration used.
- the analytical LC/MS method used in Examples 1-20 employed an Agilent 1200 with Variable Wavelength detector extracted at 220 nm and Agilent 6140 Single quadrupole mass spectrometer.
- the HPLC column was a Zorbax SB-C18, 3.5 ⁇ , 2.1 mm x 30 mm, maintained at 40 °C.
- the HPLC Gradient was 0.4 mL/min, 95:5:0.1
- 6-Bromo-2-hydroxy-naphthalene-l-carbaldehyde la 150 mg, 0.6 mmol
- morpholin-4- yl-pyrrolidin-3-yl-methanone 158 mg, 0.72 mmol
- sodium-tert-butoxide 207 mg, 2.16 mmol
- tra-(dibenzylideneacetone)dipalladium(0) 38 mg, 41 ⁇
- (2-biphenyl)di-tert- butylphosphine 25 mg, 84 ⁇
- dichloromethane (10 mL, distilled from CaH 2 ) was added to a stirred solution of titanium tetrachloride (0.67 mL, 3.39 mmol) and dichloromethyl methyl ether (0.62 mL, 6.09 mmol) in dichloromethane (10 mL, distilled from Ca3 ⁇ 4) at 0°C, and the mixture was stirred at 0°C for 1 h, then at room temperature overnight.
- 1 N hydrochloric acid (20 mL) was then added; the organic layer was separated and extracted with 1 N hydrochloric acid (2 x 20 mL). The organic layer was washed with 10 mL of saturated sodium bicarbonate , dried over magnesium sulfate and evaporated to dryness.
- the crude product was purified by column chromatography on silica gel, eluting with dichloromethane to afford lib (190 mg, 0.66 mmol, 32%).
- reaction mixture was stirred at 100 °C under argon for 1 h.
- the reaction mixture was evaporated to dryness and the solid residue was partitioned between dichloromethane and water.
- the organic phase was separated, and the aqueous layer was extracted once more with chloroform.
- the combined organic phases were dried over sodium sulfate, filtered and evaporated.
- the residue was purified by column chromatography with chloroform:methanol as eluent.
- the crude product was triturated with diethyl ether, filtered off and air dried, affording 13-1 (45 mg, 0.11 mmol, 22%).
- reaction mixture was washed with 30 mL of chloroform, the aqueous layer was cooled to 0 °C and 6N hydrochloric acid was added dropwise. The precipitating solid was filtered, washed with distilled water to afford 18-1. (675 mg, 2.16 mmol, 84%).
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Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/505,530 US9493435B2 (en) | 2009-11-03 | 2010-11-01 | IRE-1α inhibitors |
ES10828948T ES2782357T3 (en) | 2009-11-03 | 2010-11-01 | IRE 1 alpha inhibitors |
MX2012005189A MX2012005189A (en) | 2009-11-03 | 2010-11-01 | Ire-1 î± inhibitors. |
EP10828948.9A EP2496230B1 (en) | 2009-11-03 | 2010-11-01 | Ire-1 alpha inhibitors |
CA2780149A CA2780149C (en) | 2009-11-03 | 2010-11-01 | Ire-1.alpha. inhibitors |
CN201080054132.2A CN102724975B (en) | 2009-11-03 | 2010-11-01 | IRE-1 alpha inhibitor |
JP2012537926A JP5946409B2 (en) | 2009-11-03 | 2010-11-01 | IRE-1α inhibitor |
US15/349,872 US9856266B2 (en) | 2009-11-03 | 2016-11-11 | IRE-1alpha inhibitors |
US15/823,411 US20180072745A1 (en) | 2009-11-03 | 2017-11-27 | IRE-1alpha INHIBITORS |
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US25769609P | 2009-11-03 | 2009-11-03 | |
US61/257,696 | 2009-11-03 |
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US13/505,530 A-371-Of-International US9493435B2 (en) | 2009-11-03 | 2010-11-01 | IRE-1α inhibitors |
US15/349,872 Continuation US9856266B2 (en) | 2009-11-03 | 2016-11-11 | IRE-1alpha inhibitors |
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EP (1) | EP2496230B1 (en) |
JP (2) | JP5946409B2 (en) |
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CA (2) | CA3042107C (en) |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3404021A4 (en) * | 2016-01-12 | 2019-09-11 | Nippon Chemiphar Co., Ltd. | Voltage-dependent t-type calcium channel inhibitor |
KR20240046082A (en) | 2022-09-30 | 2024-04-08 | 한미약품 주식회사 | Novel tricyclic heterocyclic carbaldehyde compound and pharmaceutical composition for inhibiting IRE1α including the same |
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US9493435B2 (en) * | 2009-11-03 | 2016-11-15 | Mannking Corporation | IRE-1α inhibitors |
WO2012109238A2 (en) | 2011-02-07 | 2012-08-16 | President And Fellows Of Harvard College | Methods for increasing immune responses using agents that directly bind to and activate ire-1 |
WO2013134774A1 (en) | 2012-03-09 | 2013-09-12 | Cornell University | Modulation of breast cancer growth by modulation of xbp1 activity |
ES2724300T3 (en) | 2013-09-25 | 2019-09-10 | Univ Cornell | Compounds for inducing antitumor immunity and methods thereof |
US11234044B2 (en) | 2018-12-28 | 2022-01-25 | Sony Group Corporation | Transmission apparatus, transmission method, encoding apparatus, encoding method, reception apparatus, and reception method |
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WO2007101224A2 (en) * | 2006-02-27 | 2007-09-07 | The Board Of Trustees Of The Leland Stanford Junior University | Inhibitors of the unfolded protein response and methods for their use |
US20090186893A1 (en) * | 2007-06-08 | 2009-07-23 | Mannkind Corporation | IRE-1alpha INHIBITORS |
WO2010031056A2 (en) * | 2008-09-15 | 2010-03-18 | The Regents Of The University Of California | Methods and compositions for modulating ire1, src, and abl activity |
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US3053831A (en) * | 1961-05-05 | 1962-09-11 | American Home Prod | Dialkoxynaphthyl penicillins |
FR2763335B1 (en) * | 1997-05-16 | 2000-11-24 | Adir | NOVEL SUBSTITUTED HETEROCYCLIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
WO2011047384A2 (en) | 2009-10-16 | 2011-04-21 | The Regents Of The University Of California | Methods of inhibiting ire1 |
US9493435B2 (en) | 2009-11-03 | 2016-11-15 | Mannking Corporation | IRE-1α inhibitors |
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2010
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- 2010-11-01 CA CA3042107A patent/CA3042107C/en active Active
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- 2010-11-01 CN CN201080054132.2A patent/CN102724975B/en not_active Expired - Fee Related
- 2010-11-01 MX MX2012005189A patent/MX2012005189A/en not_active Application Discontinuation
- 2010-11-01 CA CA2780149A patent/CA2780149C/en not_active Expired - Fee Related
- 2010-11-01 EP EP10828948.9A patent/EP2496230B1/en active Active
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WO2007101224A2 (en) * | 2006-02-27 | 2007-09-07 | The Board Of Trustees Of The Leland Stanford Junior University | Inhibitors of the unfolded protein response and methods for their use |
US20090186893A1 (en) * | 2007-06-08 | 2009-07-23 | Mannkind Corporation | IRE-1alpha INHIBITORS |
WO2010031056A2 (en) * | 2008-09-15 | 2010-03-18 | The Regents Of The University Of California | Methods and compositions for modulating ire1, src, and abl activity |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3404021A4 (en) * | 2016-01-12 | 2019-09-11 | Nippon Chemiphar Co., Ltd. | Voltage-dependent t-type calcium channel inhibitor |
US11420944B2 (en) | 2016-01-12 | 2022-08-23 | Nippon Chemiphar Co., Ltd. | Voltage-dependent t-type calcium channel blocker |
KR20240046082A (en) | 2022-09-30 | 2024-04-08 | 한미약품 주식회사 | Novel tricyclic heterocyclic carbaldehyde compound and pharmaceutical composition for inhibiting IRE1α including the same |
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MX2012005189A (en) | 2012-06-12 |
CN102724975B (en) | 2015-12-02 |
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US20120270877A1 (en) | 2012-10-25 |
EP2496230A1 (en) | 2012-09-12 |
CA2780149C (en) | 2019-06-18 |
US20170166576A1 (en) | 2017-06-15 |
US9493435B2 (en) | 2016-11-15 |
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WO2011056744A4 (en) | 2011-07-14 |
JP5946409B2 (en) | 2016-07-06 |
US20180072745A1 (en) | 2018-03-15 |
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US9856266B2 (en) | 2018-01-02 |
JP2016185947A (en) | 2016-10-27 |
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