IP Library › Granted Patent US 12,344,631
Granted Patent B2
US 12,344,631 · App. 16/933,635 · Granted Jul 1, 2025

C17 polar-substituted heteroaromatic synthetic triterpenoids and methods of use thereof

Inventors: Xin Jiang (Coppell, TX); Christopher F. Bender (Garland, TX); Ha Do (Irving, TX); Haizhou Sun (Irving, TX); Melean Visnick (Irving, TX)
Assignee: REATA PHARMACEUTICALS, INC.
C07J53/002A61K9/0014A61K9/0019A61K9/0053
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Quick Facts
Patent No.
US 12,344,631
App. No.
16/933,635
Granted
Jul 1, 2025
Kind
B2
Abstract

Disclosed herein are compounds of the formula: wherein the variables are defined herein. Also provided are pharmaceutical compositions thereof. In some aspects, the compounds and compositions provided herein may be used as antioxidant inflammation modulators. In some aspects, the present disclosure provides methods wherein the compounds and composition described herein are used for the treatment of diseases and disorders, including those associated with inflammation and cancer.

Claims (25)

1. A compound of the formula:

wherein:

R 1 is a monopolar-substituted alkyl (C≤3) wherein the monopolar substituent is —F;

R 2 is hydrogen or methyl; and

R 2 ′ is methyl;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein the compound is further defined:

wherein:

R 1 is a monopolar-substituted alkyl (C≤3) wherein the monopolar substituent is —F;

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , wherein the compound is further defined:

wherein:

R 1 is a monopolar-substituted alkyl (C≤3) wherein the monopolar substituent is —F;

or a pharmaceutically acceptable salt thereof.

4. The compound of claim 1 , wherein R 1 is fluoromethyl.

5. The compound of claim 1 , further defined as:

or a pharmaceutically acceptable salt of either of these formulas.

6. The compound of claim 1 , further defined as:

or a pharmaceutically acceptable salt thereof.

7. The compound of claim 1 , further defined as:

or a pharmaceutically acceptable salt thereof.

8. A pharmaceutical composition comprising:

(A) a compound of claim 1 ; and

(B) an excipient.

9. The pharmaceutical composition of claim 8 , wherein the pharmaceutical composition is formulated for administration orally, intraadiposally, intraarterially, intraarticularly, intracranially, intradermally, intralesionally, intramuscularly, intranasally, intraocularly, intrapericardially, intraperitoneally, intrapleurally, intraprostatically, intrarectally, intrathecally, intratracheally, intratumorally, intraumbilically, intravaginally, intravenously, intravesicularlly, intravitreally, liposomally, locally, mucosally, parenterally, rectally, subconjunctival, subcutaneously, sublingually, topically, transbuccally, transdermally, vaginally, in crèmes, in lipid compositions, via a catheter, via a lavage, via continuous infusion, via infusion, via inhalation, via injection, via local delivery, or via localized perfusion.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Apr 9, 2025
From: BIOPHARMA CREDIT PLC
To: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
Reel/Frame 070793/0130 →
RELEASE OF SECURITY INTEREST Recorded Apr 9, 2025
From: BIOPHARMA CREDIT PLC
To: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
Reel/Frame 070793/0228 →
AMENDED AND RESTATED PATENT SECURITY AGREEMENT Recorded Jul 12, 2023
From: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
To: BIOPHARMA CREDIT PLC
Reel/Frame 064264/0557 →
PATENT SECURITY AGREEMENT Recorded May 18, 2023
From: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
To: BIOPHARMA CREDIT PLC
Reel/Frame 063697/0461 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 5, 2020
From: JIANG, XIN; BENDER, CHRISTOPHER F.; VISNICK, MELEAN; DO, HA; SUN, HAIZHOU
To: REATA PHARMACEUTICALS, INC.
Reel/Frame 053408/0192 →
Continuity (3)
Provisional Application 62952048 · Dec 20, 2019
Provisional Application 62876467 · Jul 19, 2019
Related Publication 20210040142A1 · Feb 11, 2021
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Clinicaltrial.gov Study NCT02657356, “Bardoxolone Methyl in Patients With Connective Tissue Disease-associated Pulmonary Arterial Hypertension—Catalyst,” and associated updates, first published Jan. 15, 2016. [cited by applicant]
Clinicaltrial.gov Study NCT03019185, “A Phase 2/3 Trial of the Efficacy and Safety of Bardoxolone Methyl in Patients With Alport Syndrome—Cardinal,” and associated updates, first published Jan. 12, 2017. [cited by applicant]
Clinicaltrial.gov Study NCT03068130, “Extended Access Program to Assess Long-term Safety of Bardoxolone Methyl in Patients With Pulmonary Hypertension Ranger,” and associated updates, first published Mar. 1, 2017. [cited by applicant]
Clinicaltrial.gov Study NCT03264079, “Effect of Itraconazole on the Pharmacokinetics of Bardoxolone Methyl in Healthy Adults,” and associated updates, first published Aug. 28, 2017. [cited by applicant]
Clinicaltrial.gov Study NCT03366337, “A Phase 2 Trial of the Safety and Efficacy of Bardoxolone Methyl in Patients With Rare Chronic Kidney Diseases—Phoenix,” and associated updates, first published Dec. 8, 2017. [cited by applicant]
Clinicaltrial.gov Study NCT03593499, “Expanded Access to Omaveloxolone for Melanoma for Patients Previously Enrolled in 408-C-1401,” and associated updates, first published Jul. 20, 2018. [cited by applicant]
Clinicaltrial.goy Study NCT03664453, “A Pharmacokinetic Study of Omaveloxolone in Healthy Volunteers,” and associated updates, first published Sep. 10, 2018. [cited by applicant]
Clinicaltrial.gov Study NCT03749447, “An Extended Access Program for Bardoxolone Methyl in Patients With CKD (EAGLE),” and associated updates, first published Nov. 21, 2018. [cited by applicant]
Clinicaltrial.gov Study NCT03902002, “A Pharmacokinetic Study of Omaveloxolone in Subjects With Hepatic Impairment and Normal Hepatic Function,” and associated updates, first published Apr. 3, 2019. [cited by applicant]
Clinicaltrial.gov Study NCT03918447, “A Trial of Bardoxolone Methyl in Patients With ADPKD—Falcon,” and associated updates, first published Apr. 17, 2019. [cited by applicant]
Clinicaltrial.gov Study NCT03931590, “A Human AME Study for Omaveloxolone,” and associated updates, first published Apr. 30, 2019. [cited by applicant]
Clinicaltrial.gov Study NCT04008186, “A Clinical Drug-Drug Interaction (DDI) Study With Omaveloxolone,” and associated updates, first published Jul. 4, 2019. [cited by applicant]
Cohen et al., “A general method for removal of a 4-methyl group from triterpenoids. Synthesis of 4β-demethylglycyrrhetinic acid,” [cited by applicant]
Connolly et al., “Grandiofolione: a novel tetranortriterpenoid,” [cited by applicant]
Couch et al., “2-cyano-3,12-dioxooleana-1,9(11)-diene-28-oic acid disrupts microtubule polymerization: a possible mechanism contributing to apoptosis,” [cited by applicant]
Couch et al., “Studies on the reactivity of CDDO, a promising new chemopreventive and chemotherapeutic agent: implications for a molecular mechanism of action,” [cited by applicant]
Damsté et al., “A sedimentary tetrahydrophenanthrene derivative of tetrahymanol,” [cited by applicant]
De Mico et al., “A Versatile and Highly Selective Hypervalent Todine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds,” [cited by applicant]
Dean et al., “Halogenolysis of metbyl glycyrrhetate with lithium iodidedimethylformamide,” [cited by applicant]
Deng and Snyder, “Preparation of a 24-Nor-1,4-dien-3-one triterpene derivative from betulin: a new route to 24-nortriterpene analogues,” [cited by applicant]
Dezube et al., “Interim results of a phase I trial with a novel orally administered synthetic triterpenoid RTA 402 (CDDO-Me) in patients with solid tumors and lymphoid malignancies,” [cited by applicant]
Dinkova-Kostova et al., “Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants,” [cited by applicant]
Dinkova-Kostova et al., “Extremely potent triterpenoid inducers of the phase 2 response: correlations of protection against oxidant and inflammatory stress,” [cited by applicant]
Dirsch et al., “The triterpenoid quinonemethide pristimerin inhibits induction of inducible nitric oxide synthase in murine macrophages,” [cited by applicant]
Dracinsky et al., “Preparation and Conformational Study of 19β,28-Epoxy-18α-olean-5-ene Derivatives,” [cited by applicant]
Dragnev et al., “Specific chemopreventive agents trigger proteasomal degradation of G1 cyclins: implications for combination therapy,” [cited by applicant]
Duan et al., “Di- and triterpenoids from Triptergium hypoglaucum,” [cited by applicant]
Duan et al., “Immunosuppressive terpenoids from extracts of tripterygium wilfordii,” [cited by applicant]
Dulubova et al., “RTA 1701 is an orally-bioavailable, potent, and selective RORγt inhibitor that suppresses Th17 differentiation in vitro and is efficacious in mouse models of autoimmune disease,” [cited by applicant]
Elliot et al., “The triterpenoid CDDO inhibits expression of matrix metalloproteinase-1, matrix metalloproteinase-13 and Bel-3 in primary human chondrocytes,” [cited by applicant]
Elsawa et al., “Preferential Inhibition of Malignant Cell Growth by CDDO in Waldenstrom Macroglobulinemia,” [cited by applicant]
Favaloro et al., “Design and synthesis of tricyclic compounds with enone functionalities in rings A and C: a novel class of highly active inhibitors of nitric oxide production in mouse macrophages,” [cited by applicant]
Finlay et al., “Novel A-ring cleaved analogs of oleanolic and arsolic acids which affect growth regulation in NRP.152 prostate cells,” [cited by applicant]
Finlay et al., “The Effect of A and C Ring Modification of Oleanolic and Ursolic Acid on the Inhibition of Nitric Oxide Formation in Mouse Macrophages,” 213th American Chemical Society National Meeting, Abstract: 084, 1… [cited by applicant]
Gaffen et al., “IL-23-IL-17 immune axis: discovery, mechanistic understanding, and clinical testing”, [cited by applicant]
Gao et al., “Synthetic triterpenoids inhibit growth and induce apoptosis in human glioblastoma and neuroblastoma cells through inhibition of prosurvival Akt, NF-κB and Notch1 signaling,” [cited by applicant]
Grant et al., “Boron trifluoride catalyzed rearrangements of novel epoxide derivatives of manool and manoyl oxide,” [cited by applicant]
Grieco and Speake, “Synthetic Studies on Quassinoids: Total Synthesis and Biological Evaluation of (+)-Des-D-chaparrinone,” [cited by applicant]
Guix et al., “The physiology and pathophysiology of nitric oxide in the brain”, [cited by applicant]
Hail et al., “Evidence supporting a role for calcium in apoptosis induction by the synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO),” [cited by applicant]
Han et al., “CDDO-Imidazolide inhibits growth and survival of c-Myc-induced mouse B cell and plasma cell neoplasms,” [cited by applicant]
Hayes and McMahon, “NRF2 and KEAP1 mutations: permanent activation of an adaptive response in cancer”, [cited by applicant]
Hill et al., “Synthetical approaches to the pristimerin chromophore,” [cited by applicant]
Hirota et al., “Suppression of tumor promoter-induced inflammation of mouse ear by ursolic acid and 4,4-dimethycholestane derivatives,” [cited by applicant]
Hirota et al., “Total synthesis of (±)-amarolide, a quassinoid bitter principle,” [cited by applicant]
Honda et al., “A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production,” [cited by applicant]
Honda et al., “An efficient synthesis of tricyclic compounds (+)-(4aβ, 8aβ, 10α)-1,2,3,4,4a,6,7,8,8a,9,1-,10a-Dodecahydro-1,1,4a-Trimethyl-2-Oxophenanthrene-8a-Carboxolic acid, its methyl ester, and (+)-(4aβ,8aβ, 10aα)-… [cited by applicant]
Honda et al., “Design and synthesis of 23, 24-dinoroleanolic acid derivatives, novel triterpenoid-steroid hybrid molecules,” [cited by applicant]
Honda et al., “Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages,” [cited by applicant]
Honda et al., “Design, synthesis, and biological evaluation of biotin conjugates of 2-cyano-3,12-dioxooleana˜1,9(11)-dien-28-oic acid for the isolation of the protein targets,” [cited by applicant]
Honda et al., “Efficient synthesis of (−)- and (+)-tricyclic compounds with enome functionalities in rings A and C. A novel class of orally active anti-inflammatory and cancer chemopreventive agents,” [cited by applicant]
Honda et al., “New enone derivatives of oleanolic acid and ursolic acid as inhibitors of nitric oxide production in mouse macrophages,” [cited by applicant]
Honda et al., “New synthetic oleanane and arsane triterpenoids as inhibitors of nitric oxide production in mouse macrophages,” The Fifth Chemical Congress of North America, Cancun, Mexico, Abstract 552 and slides for or… [cited by applicant]
Honda et al., “Novel synthetic oleanane and ursane triterpenoids with various enone functionalities in ring A as inhibitors of nitric oxide production in mouse macrophages,” [cited by applicant]
Honda et al., “Novel synthetic oleanane triterpenoids: a series of highly active inhibitors of nitric oxide production in mouse macrophages,” [cited by applicant]
Honda et al., “Novel tricyclic compounds having acetylene groups at C-8a and cyano enones in rings A and C: highly potent anti-inflammatory and cytoprotective agents,” [cited by applicant]
Honda et al., “Revision and confirmation of the regiochemistry of isoxazoles derived from methyl oleanonate and lanost-8-en-3-one. Synthesis of a new lanostane triterpenoid with a cyano-enone functionality in ring A,” [cited by applicant]
Honda et al., “Synthesis of (±)-3,3-ethylenedioxy-14a-hydroxy-S-picrasene-11,16-dione, a 14aH-picrasane derivative,” [cited by applicant]
Honda et al., “Synthesis of a novel dicyano abietane analogue: a potential antiinflammatory agent,” [cited by applicant]
Honda et al., “Synthetic oleanane and ursane triterpenoids with modified rings A and C: A series of highly active inhibitors of nitric oxide production in mouse macrophages,” J. Med. Chem., 43:4233-4246, 2000. [cited by applicant]
Hong et al., “Phase I trial of a novel oral NF-κB/pSTAT3 inhibitor RTA-402 in patients with solid tumors and lympboid malignancies,” 44th Annual Meeting of the American Society of Clinical Oncology, 2008. [cited by applicant]
Hu et al., “The IL-17 pathway as a major therapeutic target in autoimmune diseases”, [cited by applicant]
Huerta et al., “Characterization of novel small-molecule NRF2 activators: Structural and biochemical validation of stereospecific KEAP1 binding,” [cited by applicant]
Hyer et al., “Synthetic triterpenoids cooperate with tumor necrosis factor-related apoptosis-inducing ligand to induce apoptosis of breast cancer cells,” [cited by applicant]
Ikeda et al., “Induction of redox imbalance and apoptosis in multiple myeloma cells by the novel triterpenoid 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid,” [cited by applicant]
Ikeda et al., “The novel triterpenoid CDDO and its derivatives induce apoptosis by disruption of intracellular redox balance,” [cited by applicant]
Ikeda et al., “Triterpenoid CDDO-Im downregulates PML/RAR αexpression in acute promyelocytic leukemia cell,” [cited by applicant]
Inoue et al., “CDDO induces apoptosis via the intrinsic pathway in lymphoid cells,” [cited by applicant]
International Search Report and Written Opinion issued in corresponding PCT Application No. PCT/US2020/042788, mailed on Oct. 23, 2020. [cited by applicant]
Ito et al., “Involvement of caspase-8 in the induction of osteosarcoma cell apoptosis by the novel triterpenoid CDDO,” 47th Annual Meeting, Orthopaedic Research Society, Feb. 25-28, 2001, San Francisco, California, p. 0… [cited by applicant]
Ito et al., “The novel triterpenoid 2-cyano-3, 12-dioxoolean-1,9-dien-28-oic acid induces apoptosis of human myeloid leukemia cells by a caspase-8-dependent mechanism,” [cited by applicant]
Ito et al., “The novel triterpenoid CDDO induces apoptosis and differentiation of human osteosarcoma cells by a caspase-8 dependent mechanism,” [cited by applicant]
Ivanov et al., “The orphan nuclear receptor RORγt directs the differentiation program of proinflammatory IL-17+ T helper cells”, [cited by applicant]
Iwakura and Ishigame, “The IL-23/IL-17 axis in inflammation”, 116(5):1218-1222, 2006. [cited by applicant]
Jang et al., “24-nor-ursane type triterpenoids from the stems of Rumex japonicus,” [cited by applicant]
Ji et al., “The synthetic triterpenoid CDDO-imidazolide induces monocytic differentiation by activating the Smad and ERK signaling pathways in HL60 leukemia cells,” [cited by applicant]
Johansen et al., “Pharmacology and preclinical pharmacokinetics of the triterpenoid CDDO methyl ester,” [cited by applicant]
Johns et al., “Triterpenes of [cited by applicant]
Kahne and Collum, “Kinetic cyanations of ketone enolates,” [cited by applicant]
Kamal et al., “23-oxoisopristimerin III: an new natural phenolic (9→8)-24-nor-D:A-friedo-oleanane triterpene,” [cited by applicant]
Kamal et al., “Structures of two new phenolic 24-nor-D: A-friedoleananes related to zeylasterone: a partial synthesis of trimethylzeylasterone,” [cited by applicant]
Kamal et al., “The structure of zeylasterone, the first of a new series of phenolic 24-nor-D: A friedo-oleanane triterpenes,” [cited by applicant]
Kansanen et al., “Regulation of Nrf2-dependent gene expression by 15-deoxy-Δ12,14-prostaglandin J2,” [cited by applicant]
Khalid et al., “Isolation and characterization of pristimerin as the antiplasmodial and antileishmanial agent of maytenus senegalensis (Lam.) Exell,” [cited by applicant]
Kim et al., “An inducible pathway for degradation of FLIP protein sensitizes tumor cells to TRAIL-induced apoptosis,” [cited by applicant]
Kim et al., “Caspase-3 activation is involved in apoptosis induced by a synthetic triterpenoid in Non-small cell lung cancer (NSCLC) cells,” [cited by applicant]
Kim et al., “Identification of a novel synthetic triterpenoid, methyl-2-cyano-3,12-dioxooleana-1,9-dien-28-oate, that potently induces caspase-mediated apoptosis in human lung cancer cells,” [cited by applicant]
Kincl et al., “Pituitary gonadotropin inhibitory action of neutral steroids,” [cited by applicant]
Kircher, “Triterpenes, in organ pipe cactus,” Phytochemistry, 19:2707-2712, 1980; Database CAPLUS on STN AN:1981:550946. [cited by applicant]
Klyne et al., “The molecular rotations of polyclyclic compounds. III. Polyelyclic alcohols and their derivatives,” [cited by applicant]
Kobayashi et al., “The antioxidant defense system Keap1-Nrf2 comprises a multiple sensing mechanism for responding to a wide range of chemical compounds,” [cited by applicant]
Kolak et al., “Antioxidant and anticholinesterase constituents of Salvia poculata,” [cited by applicant]
Konopleva et al., “Activation of nuclear transcription factor PPARγ by the novel triterpenoid CDDO as targeted therapy in breast cancer,” 2002 Keystone Symposium, Abstract No. 539, 2002. [cited by applicant]
Konopleva et al., “Mechanisms and Activity of PPARγ-Active Triterpenoids CDDO and CDDO-Me in Leukemias,” [cited by applicant]
Konopleva et al., “Novel synthetic triterpenoid CDDO-Me: potent antiproliferative, proapoptotic and differentiating agent in AML,” [cited by applicant]
Konopleva et al., “Novel synthetic triterpenoid, CDDO, and its methyl ester: Potent antiproliferative, proapoptotic and differentiating agents in AML,” [cited by applicant]
Konopleva et al., “Novel triterpenoid CDDO-Me is a potent inducer of apoptosis and differentiation in acute myelogenous leukemia,” [cited by applicant]
Konopleva et al., “Peroxisome proliferator-activated receptor γand retinoid X receptor ligands are potent inducers of differentiation and apoptosis in leukemias,” [cited by applicant]
Konopleva et al., “PPARγ Ligand CDDO Induces Apoptosis in Leukemias Via Multiple Apoptosis Pathways,” Abstracts of the 44th Annual Meeting of the American Society of Hematology, Abstract No. 2209, 2002. [cited by applicant]
Konopleva et al., “PPARγ Ligands Are Potent Inducers of Apoptosis in Leukemias and Lymphomas,” American Society of Hematology 43rd Annual Meeting and Exposition, Abstract No. 501, 2001. [cited by applicant]
Konopleva et al., “PPARγ Nuclear Receptor as a Novel Molecular Target in Leukemia Therapy,” [cited by applicant]
Konopleva et al., “PPARγ nuclear receptor as a novel therapeutic target in AML,” Blood, 96(11):460a, Abstract #1982, 2000. [cited by applicant]
Konopleva et al., “PPARγ nuclear receptor as a novel therapeutic target in AML,” Proc. of the AACR, 42, Abstract #4458, 2001. [cited by applicant]
Konopleva et al., “Suppression of ERK Activation is Required for Triterpenoid Methyl-CDDO-Induced Apoptosis in AML,” [cited by applicant]
Konopleva et al., “Synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid induces growth arrest in HER2-overexpressing breast cancer cells,” [cited by applicant]
Konopleva et al., “Synthetic triterpenoid CDDO as a novel therapy for resistant breast cancer,” [cited by applicant]
Konopleva et al., “The novel triterpenoid CDDO-Me suppresses MAPK pathways and promotes p38 activation in acute myeloid leukemia cells,” [cited by applicant]
Konopleva et al., “The synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid induces caspase-dependent and -independent apoptosis in acute myelogenous leukemia,” [cited by applicant]
Korovin and Tkachev, “Synthesis of quinoxalines fused with triterpenes, ursolic acid and betulin derivatives,” [cited by applicant]
Koschmieder et al. “CDDO induces granulocytic differentiation of myeloid leukemic blasts through translational up-regulation of p42 CCAAT enhancer-binding protein alpha,” [cited by applicant]
Kress et al., “Triterpenoids display single agent activity in a mouse model of CLL/SBL,” [cited by applicant]
Kress et al., “Triterpenoids display single agent anti-tumor activity in a transgenic mouse model of chronic lymphocytic leukemia and small B cell lymphoma,” [cited by applicant]
Kurinna et al., “The novel triterpenoid CDDO-Me promotes apoptosis in Gleevec-resistant chronic myeloid leukemia cells by caspase-independent mechanisms,” [cited by applicant]
Kutschabsky et al., “Molecular and crystal structure of a new 24-nor triperpenoid carboxylic acid from Acanthopanax trifoliatus,” [cited by applicant]
Lapillonne et al., “Activation of peroxisome proliferator-activated receptor γ by a novel synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid induces growth arrest and apoptosis in breast cancer cells,” [cited by applicant]
Larock et al., “Carbocycle synthesis via carbopalladation of nitriles,” [cited by applicant]
Lavie et al., “Studies on epoxides. IV. Rearrangements in triterpenoids,” [cited by applicant]
Lavie et al., “Tetranortriterpenoids from Melia azadirachta,” [cited by applicant]
Lei et al., “Regulatory T cell-mediated anti-inflammatory effects promote successful tissue repair in both indirect and direct manners,” [cited by applicant]
Li and Förstermann, “Nitric oxide in the pathogenesis of vascular disease”, [cited by applicant]
Li et al., “Terpenoids from tripterygium wilfordii,” [cited by applicant]
Liby et al., “Novel semisynthetic analogues of betulinic acid with diverse cytoprotective, antiproliferative, and proapoptotic activities,” [cited by applicant]
Liby et al., “The rexinoid LG100268 and the synthetic triterpenoid CDDO-methyl amide are more potent than erlotinib for prevention of mouse lung carcinogenesis,” [cited by applicant]
Liby et al., “The synthetic triterpenoid CDDO-Imidazolide suppresses STAT phosphory lation and induces apoptosis in myeloma and lung cancer cells,” [cited by applicant]
Liby et al., “The synthetic triterpenoids CDDO-Methyl ester and CDDO-ethyl amide prevent lung cancer induced by vinyl carbamate in A/J mice,” [cited by applicant]
Liby et al., “The synthetic triterpenoids, CDDO and CDDO-imidazolide, are potent inducers of here oxygenase-1 and Nrf2/ARE signaling,” [cited by applicant]
Liby et al., “Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer,” [cited by applicant]
Ling et al., “The novel triterpenoid C-28 methyl ester of 2-cyano-3, 12-dioxoolen-1, 9-dien-28-oic acid inhibits metastatic murine breast tumor growth through inactivation of STAT3 signaling,” [cited by applicant]
Ling et al., “The novel triterpenoid CDDO-Me inhibits metastatic murine breast tumor through inhibition of Stat3 signaling,” 2007 AACR Annual Meeting, Abstract No. 301, 2007. [cited by applicant]
Liu et al,. “New lupane-type triterpenoid saponins from leaves of [cited by applicant]
Liu et al., “Chemical constituents from root of rubus irenaeus,” [cited by applicant]
Marples and Spilling, “Ene reactions of unsaturated acyloins,” [cited by applicant]
Marples and Spilling, “Facile intramolecular ene reactions of steroidal unsaturated acyloins,” [cited by applicant]
Martinez et al., “Regulation and Function of Proinflammatory TH17 Cells,” [cited by applicant]
Melichar et al., “Growth-inhibitory effect of a novel synthetic triterpenoid, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, on ovarian carcinoma cell lines not dependent on peroxisome proliferator-activated receptor-γ e… [cited by applicant]
Mencherini et al., “Triterpenoid constituents from the roots of the [cited by applicant]
Minns et al., “A novel triterpenoid induces transforming growth factor β production by intraepithelial lymphocytes to prevent ileitis,” [cited by applicant]
Mix et al., “A synthetic triterpenoid selectively inhibits the induction of matrix metalloproteinases 1 and 13 by inflammatory cytokines,” [cited by applicant]
Mix et al., “Peroxisome proliferator-activated receptor-γ-independent repression of collagenase gene expression by 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid and prostaglandin 15-deoxy-delta(12,14) J2: a role for Sma… [cited by applicant]
Murphy et al., “Immunomodulatory Effects of the Triterpenoid CDDO after Allogeneic Bone Marrow Transplantation in Mice: Reduction of Acute Graft-Versus-Host Disease Lethality,” [cited by applicant]
Murray and Zweifel, “Preparation of Phenyl Cyanate and Its Utilization for the Synthesis of α, β-Unsaturated Nitriles,” [cited by applicant]
Muzart, “Synthesis of unsaturated carbonyl compounds via a chromium-mediated allylic oxidation by 70% tert.butylhydroperoxide,” [cited by applicant]
Na and Surh et al., “Transcriptional regulation via cysteine thiol modification: a novel molecular strategy for chemoprevention and cytoprotection,” [cited by applicant]
Nair et al., “Triterpenes. XLVII. Oxidation rates of triterpenoid secondary alcohols with chromic acid,” [cited by applicant]
Nanduri et al., “Biological investigation and structure-activity relationship studies on azadirone from azadirachta indica [cited by applicant]
Nelson et al., “Oxidative demethylation at C-4 of a steroid via nitroxide photolysis,” [cited by applicant]
Niikura et al., “The effects of synthetic triterpenoids on superficial zone protein synthesis in articular chondrocytes,” Abstract, [cited by applicant]
Niikura et al., “The effects of synthetic triterpenoids on szp synthesis in articular chondrocytes,” Abstract P197, [cited by applicant]
Nishimura et al., “Activity-guided isolation of triterpenoid acyl CoA cholesteryl acyl transferase (ACAT) inhibitors from Ilex kudincha,” [cited by applicant]
Nishino et al., “Inhibition of the tumor-promoting action of 12-O tetradecanoylphorbol-13-acetate by some oleanane-type triterpenoid compounds,” [cited by applicant]
Osburn et al., “Genetic of pharmacologic amplification of Nrf2 signaling inhibits acute inflammatory liver injury in mice,” [cited by applicant]
Ovemell and Whitehurts, “Reactions of steroid A-ring lactones with Grignard reagents,” [cited by applicant]
Pappas et al., “Photoisomerization of phenalen-1-one oxide. New course of light-induced alpha beta-epoxy ketone rearrangement,” [cited by applicant]
Peakman et al., “Characterization of 24-nor-triterpenoids occurring in sediments and crude oils by comparison with synthesized standards,” [cited by applicant]
Pedersen et al., “The triterpenoid CDDO induces apoptosis in refractory CLL B cells,” [cited by applicant]
Place et al., “The novel synthetic triterpenoid, CDDO-imidazolide, inhibits inflammatory response and tumor growth in vivo,” [cited by applicant]
Rasmusson et al., “Azasteroids: structure-activity relationships for inhibition of 5 α-reductase and of androgen receptor binding,” [cited by applicant]
Ray et al., “The novel triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO) induces apoptosis of human diffuse large B-cell lymphoma cells through a peroxisome proliferator-activated receptor γ-independent … [cited by applicant]