- Structure-activity relationships of 4-hydroxy-3-nitroquinolin-2(1H)- ones as novel antagonists at the glycine site of N-methyl-D-aspartate receptors
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A series of 4-hydroxy-3-nitroquinolin-2(1H)-ones (HNQs) was synthesized by nitration of the corresponding 2,4-quinolinediols. The HNQs were evaluated as antagonists at the glycine site of NMDA receptors by inhibition of [3H]DCKA binding to rat brain membranes. Selected HNQs were also tested for functional antagonism by electrophysiological assays in Xenopus oocytes expressing either 1a/2C subunits of NMDA receptors or rat brain AMPA receptors. The structure-activity relationships (SAR) of HNQs showed that substitutions in the 5-, 6-, and 7-positions in general increase potency while substitutions in the 8-position cause a sharp reduction in potency. Among the HNQs tested, 5,6,7-trichloro HNQ (8i) was the most potent antagonist with an IC50 of 220 nM in [3H]DCKA binding assay and a K(b) of 79 nM from electrophysiological assays. Measured under steady-state conditions HNQ 8i is 240-fold selective for NMDA over AMPA receptors. The SAR of HNQs was compared with those of 1,4-dihydroquinoxaline-2,3-diones (QXs) and 1,2,3,4-tetrahydroquinoline-2,3,4-trione 3-oximes (QTOs). In general, HNQs have similar potencies to QXs with the same benzene ring substitution pattern but are about 10 times less active than the corresponding QTOs. HNQs are more selective for NMDA receptors than the corresponding QXs and QTOs. The similarity of the SAR of HNQs, QXs, and QTOs suggested that these three classes of antagonists might bind to the glycine site in a similar manner. With appropriate substitutions, HNQs represent a new class of potent and highly selective NMDA receptor glycine site antagonists.
- Cai, Sui Xiong,Zhou, Zhang-Lin,Huang, Jin-Cheng,Whittemore, Edward R.,Egbuwoku, Zizi O.,Hawkinson, Jon E.,Woodward, Richard M.,Weber, Eckard,Keana, John F. W.
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Read Online
- Design, synthesis, and anticonvulsant evaluation of 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones, and their derivatives
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The novel group of 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones, and their derivatives was designed as potential anticonvulsants using GABA pharmacophore and corresponding heterocyclic moieties. A number of compounds of this group were synthesized and studied in the maximum electroshock seizure (MES) test and in the model of primary-generalized convulsions caused by subcutaneous pentylenetetrazole (scPTZ) in mice. The most active compound in the MES test was found to be 1a (N-(3-nitrocoumarin-4-yl)-4-aminobutyric acid) at a dose range of 60–80 mg/kg that increased the number of survived animals up to 60% in comparison with the control group, whose survival rate was 10%. Compounds 1d (N-(3,6-dinitrocoumarin-4-yl)-4-amino-butyric acid methyl ester) at doses of 10–40 mg/kg and 3a (N-(3-nitro-2-oxo-1,2-dihydroquinolin-4-yl)-4-amino-butyric acid methyl ester) at a dose of 12.5 mg/kg had the most pronounced anticonvulsant effect in scPTZ test. [Figure not available: see fulltext.].
- Mokrov,Litvinova,Voronina,Nerobkova,Kutepova,Kovalev,Gudasheva,Durnev
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Read Online
- Imidazo quinoline substituted phosphate agonist as well as preparation method and application thereof
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The invention relates to an imidazo quinoline substituted phosphate agonist as well as a preparation method and an application thereof. Specifically, the compound disclosed by the invention has a structure as shown in a formula (I), and the definitions of all groups and substituent groups are described in the specification. The invention also discloses a preparation method of the compound and the application of the compound as a TLR agonist.
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Paragraph 0193-0198
(2021/05/12)
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- IMIDAZOQUINOLINE-TYPE COMPOUNDS AND USES THEREOF
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Provided in the present disclosure are imidazoquinoline-type compounds, methods for their preparation, pharmaceutical compositions thereof and their use, wherein the imidazoquinoline-type compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.
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Paragraph 0011; 0092; 0093
(2021/10/11)
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- Synthesis of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as potent antiproliferative agents via a hybrid pharmacophore approach
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Imiquimod (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine) is efficacious in topical therapy for certain types of skin cancers. Structurally similar EAPB0203 (N-methyl-1-(2-phenethyl)imidazo[1,2-a]quinoxalin-4-amine) has been shown higher in vitro potency than imiquimod. Besides, triazole, oxadiazole, and thiadiazole rings are privileged building blocks in drug design. A series of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole and [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-thiadiazole derivatives were therefore synthesized by incorporation of these rings into the structure of EAPB0203 and assessed their antiproliferative effects against various cancer cell lines. The 1,3,4-oxadiazole derivatives demonstrated the superior effectiveness compared to imiquimod and EAPB0203. Our findings highlight the excellent potential of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as anticancer agents.
- Kaneko, Daiki,Ninomiya, Masayuki,Yoshikawa, Rina,Ono, Yukari,Sonawane, Amol D.,Tanaka, Kaori,Nishina, Atsuyoshi,Koketsu, Mamoru
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- TLR7/8 AGONISTS AND LIPOSOME COMPOSITIONS
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The present disclosure relates to a method of loading a toll like receptor (TLR)7/8 agonist into a liposome using remote loading and a kit of parts suitable for the loading of a TLR7/8 agonist into a liposome by said method. The present disclosure further relates to a liposome comprising a salt of a TLR7/8 agonist in the liposome interior and to the use of said liposome for stimulation of an immune response and/or treatment of a clinical condition. Finally, the present disclosure relates to a TLR7/8 agonist which is suitable for being remotely loaded into a liposome.
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Page/Page column 13; 78-79
(2020/02/16)
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- PEPTIDE-BASED VACCINES, METHODS OF MANUFACTURING, AND USES THEREOF FOR INDUCING AN IMMUNE RESPONSE
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The present disclosure relates to novel peptide-based vaccines, methods of manufacturing the novel peptide-based vaccines and uses thereof for delivering peptide antigens to induce an immune response, and in particular a T cell response to a subject.
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Paragraph 0042
(2020/03/01)
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- LOCALLY ACTING TOLL-LIKE RECEPTOR 7 (TLR7) AND/OR TLR8 AGONIST IMMUNOTHERAPY COMPOUNDS AND THEIR USES
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Provided in the present disclosure are immunotherapy compounds, pharmaceutical compositions thereof and their use, wherein the immunotherapy compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.
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Paragraph 0030; 00172-00175
(2020/10/19)
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- Efficacy of TLR7 agonistic imidazoquinoline as immunochemotherapeutic agent against P. Berghei ANKA infected rodent host
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Malaria is a serious disease and is one of the most alarming public health issues. Plasmodium is being resistant to various antimalarials including Chloroquine (CQ) which was the first-line therapy for malaria treatment. WHO recommended several combination therapies but declining efficacy was reported to many of these therapies. Despite a great amount of research, efficient malaria vaccine still seems to be a distant dream. Immunochemotherapy could be an alternate strategy to deal with malaria. Based on the differential activity of various cytokines in the pathogenesis of and protection against malaria, the efficacy of highly active TLR7 agonistic imidazoquinoline (BBIQ) in combination with a suboptimal dose of CQ against P. berghei ANKA (PbA) in vivo was investigated. In mice treated with CQ alone, parasite appeared on Day 17 and all mice of this group died by Day 21. Whereas, mice treated with BBIQ along with CQ exhibited no appearance of parasite till Day 23. Frequencies of T cells (CD3+, CD4+and CD8+) and T regulatory cells (CD4+, CD25 +and FoxP3+) were found to be lower in brain of BBIQ + CQ treated mice as compared to BBIQ alone and CQ alone treated mice on Day 10. Inhibition of infiltration of inflammatory T cells and activation of T helper and T cytotoxic cells against the parasite was observed in the mice treated with this combination therapy. Serum levels of IFN-γ and IL-12 were found to be higher on same day in mice treated with BBIQ + CQ which revealed the generation of strong Th1 immune response in mice against the infection. Overall, TLR7 agonist acted as an efficient partner when combined with potent antimalarial drug.
- Saroa, Ruchika,Kaushik, Deepender,Bagai, Upma,Kaur, Sukhbir,Salunke, Deepak B.
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supporting information
p. 1099 - 1105
(2019/03/08)
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- ALKYL CHAIN MODIFIED IMIDAZOQUINOLINE TLR7/8 AGONIST COMPOUNDS AND USES THEREOF
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Disclosed are alkyl chain modified 1H-imidazoquinoline compounds, derivatives and analogs thereof, as Toll-like receptor-7 and -8 agonists for enhancing immune responses. Also provided are methods of making pharmaceutical compositions containing these compounds. The present disclosure also describes methods of use for the alkyl chain modified 1H-imidazoquinoline compounds, derivatives and analogs thereof, and pharmaceutical compositions containing these compounds for the treatment of disease in a subject.
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Paragraph 0195
(2019/03/08)
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- CLEAVABLE CONJUGATES OF TLR7/8 AGONIST COMPOUNDS, METHODS FOR PREPARATION, AND USES THEREOF
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The present disclosure relates to cleavable conjugates (for example, particle-based or antibody-based conjugates) of TLR7/8 agonists (for example, 1H-imidazo[4,5-c]quinoline derivatives) containing a conjugation linker, a cleavable linker, and a self-eliminating linker. The present disclosure also related to methods for preparation of the cleavable conjugates, uses thereof for stimulating an effective immune response, and uses thereof for the treatment of cancer.
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Paragraph 0593
(2019/06/07)
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- Imidazole quinoline-based immune system modulators
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The present invention relates to a compound of Formula I: or an enantiomer, diastereomer, tautomer, or pharmaceutically acceptable salt or solvate thereof, wherein the symbols are as defined in the specification; a pharmaceutical composition comprising the same; and a method for treating or preventing autoimmunity disease using the same.
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Page/Page column 86
(2018/02/28)
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- IMMUNOCONJUGATE SYNTHESIS METHOD
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A method for producing an immunoconjugate, the method comprising combining one or more compounds of Formula I and an antibody of Formula II, wherein Formula II is an antibody with one or more lysine residues, in an aqueous solution buffered at a pH of about 7.5 to about 9 until at least 33 mol% of the one or more compounds of Formula I is conjugated to the antibody of Formula II to provide the immunoconjugate of Formula III, wherein Adj is an adjuvant, Z is –CH2–, –C(O)NH–, –C(O)O–, or –C(O)–, L is a linker, E is an ester, and r is the average number of adjuvants attached to the antibody and is a positive number up to about 8, in a first buffered aqueous solution.
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Paragraph 0390
(2018/11/10)
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- Design, synthesis and biological evaluation of benzyloxyphenyl-methylaminophenol derivatives as STAT3 signaling pathway inhibitors
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STAT3 signaling pathway has been validated as a vital therapeutic target for cancer therapy. Based on the novel STAT3 inhibitor of a benzyloxyphenyl-methylaminophenol scaffold hit (1) discovered through virtual screening, a series of analogues had been designed and synthesized for more potent inhibitors. The preliminary SAR had been discussed and the unique binding site in SH2 domain was predicted by molecular docking. Among them, compounds 4a and 4b exhibited superior activities than hit compound (1) against IL-6/STAT3 signaling pathway with IC50 values as low as 7.71 μM and 1.38 μM, respectively. Compound 4a also displayed potent antiproliferative activity against MDA-MB-468 cell line with an IC50 value of 9.61 μM. We believe that these benzyloxyphenyl-methylaminophenol derivatives represent a unique mechanism for interrogating STAT3 as well as a potential structure type for further exploration.
- Gao, Dingding,Xiao, Qiang,Zhang, Mingming,Li, Yingxia
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p. 2549 - 2558
(2016/05/09)
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- POLYMER ADJUVANT
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The invention relates to an adjuvant comprising Pattern Recognition Receptor (PRR) agonist molecules linked to polymer chains that are capable of undergoing particle formation in aqueous conditions, or in aqueous conditions in response to external stimuli; and methods of treatment or prevention of disease using such an adjuvant.
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Page/Page column 48
(2016/05/02)
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- Dual inhibitors of epidermal growth factor receptor and topoisomerase IIα derived from a quinoline scaffold
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Based on the quinazoline bearing EGFR inhibitors, a series of thirty four compounds having a quinoline scaffold were synthesised and evaluated in vitro for EGFR kinase inhibitory activity. A structure-activity relationship study revealed that 2,4-bis(arylamino) substituted quinolines possessed better anti-EGFR kinase activity. Compounds 3f and 3m emerged as potent EGFR kinase inhibitors (200 and 210 nM, respectively) and showed excellent anticancer activity at the micromolar level against a panel of cancer cell lines comparable to erlotinib. Furthermore, representative compounds inhibited the human topoisomerase IIα selectively and catalytically, did not intercalate with DNA, increased intracellular ROS concentration (except 3m) and altered the mitochondrial membrane potential of the cancer cells. Cell cycle analysis and annexin-V staining in a lung cancer cell line showed that the compounds delayed cell cycle progression by inducing cell cycle arrest and subsequent apoptosis at the G1 phase. The facts were further corroborated through molecular modeling studies.
- Chauhan, Monika,Joshi, Gaurav,Kler, Harveen,Kashyap, Archana,Amrutkar, Suyog M.,Sharma, Praveen,Bhilare, Kiran D.,Chand Banerjee, Uttam,Singh, Sandeep,Kumar, Raj
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p. 77717 - 77734
(2018/06/22)
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- Synthesis of azabicyclo[4.2.0]octa-1,3,5-trien-8-one analogues of 1H-imidazo[4,5-c]quinoline and evaluation of their antimicrobial and anticancer activities
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In search of new and efficient antimicrobial and anticancer agents based on the imidazoquinoline structural framework, a series of novel 7-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-7-Azabicyclo[4.2.0]octa-1,3, 5-trien-8-ones (8a-f) were synthesized from the corresponding 2,4-dihydroxoquinoline derivative through multistep reactions. The structures of these compounds were established by IR, 1H NMR, 13C NMR and mass spectral studies. The 7-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-7- Azabicyclo[4.2.0]octa-1,3,5-trien-8-one (8a-f) analogues were evaluated for their in vitro antimicrobial activity by serial dilution method minimum inhibitory concentration (MIC). The derivatives 8c, 8e and 8f exhibited excellent antibacterial activity comparable to the parent drug ampicillin with MIC value. Compounds 7a-f and 8a-f were also assessed for their cytotoxic activity (IC50) against HeLa cells using the Trypan blue exclusion assay method. The compounds 7c and 8b displayed potential anticancer activity. In a molecular docking study, these compounds showed minimum binding energy and good affinity towards the active pocket. They are believed to be good inhibitors of β-tubulin. The results of these studies provided evidence that 7-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-7-Azabicyclo[4.2.0]octa-1,3, 5-trien-8-one (8a-f) derivatives are a promising class of antibacterial and anticancer agents.
- Kayarmar, Reshma,Nagaraja,Bhat, Manjunath,Naik, Prashantha,Rajesh,Shetty, Suchetha,Arulmoli
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p. 2964 - 2975
(2014/05/06)
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- Discovery of imigliptin, a novel selective DPP-4 inhibitor for the treatment of type 2 diabetes
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We report our discovery of a novel series of potent and selective dipeptidyl peptidase IV (DPP-4) inhibitors. Starting from a lead identified by scaffold-hopping approach, our discovery and development efforts were focused on exploring structure-activity relationships, optimizing pharmacokinetic profile, improving in vitro and in vivo efficacy, and evaluating safety profile. The selected candidate, Imigliptin, is now undergoing clinical trial.
- Shu, Chutian,Ge, Hu,Song, Michael,Chen, Jyun-Hong,Zhou, Huimin,Qi, Qu,Wang, Feng,Ma, Xifeng,Yang, Xiaolei,Zhang, Genyan,Ding, Yanwei,Zhou, Dapeng,Peng, Peng,Shih, Cheng-Kon,Xu, Jun,Wu, Frank
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supporting information
p. 921 - 926
(2014/09/17)
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- AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY
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Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.
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Page/Page column 177-178
(2014/08/19)
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- NOVEL IMIDAZOLE QUINOLINE-BASED IMMUNE SYSTEM MODULATORS
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The present invention relates to a compound of Formula I: or an enantiomer, diastereomer, tautomer, or pharmaceutically acceptable salt or solvate thereof, wherein the symbols are as defined in the specification; a pharmaceutical composition comprising the same; and a method for treating or preventing autoimmunity disease using the same.
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Paragraph 0220
(2013/04/24)
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- IMMUNOMODULATORY CONJUGATES
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The present invention provides an immunomodulatory compound comprising a carbohydrate polymer comprising mannose, wherein the carbohydrate polymer is conjugated to at least one immune modulator. The present invention also provides for the use of this compound in immunomodulatory compositions for vaccination and gene therapy methods, together with processes for its preparation.
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Page/Page column 77
(2013/05/23)
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- TLR-AGONIST-CONJUGATED ANTIBODY RECRUITING MOLECULES (TLR_ARMS)
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The present invention relates to chimeric chemical compounds which are used to recruit antibodies to cancer cells, in particular, prostate cancer cells or metastasized prostate cancer cells. The compounds according to the present invention comprise an antibody binding terminus (ABT) moiety covalently bonded to a cell binding terminus (CBT) and Toll-like receptor agonist (TLR) through a linker and a multifunctional connector group or molecule.
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- Synthesis and antikinetoplastid activities of 3-substituted quinolinones derivatives
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A new family of quinolinone derivatives has been synthesized and evaluated for their antikinetoplastid activities against Leishmania donovani and Trypanosoma brucei brucei. Results from these structure-activity relationship studies enabled identification of compounds 3a and 4g as the most active compounds against L. donovani promastigotes and amastigotes parasites (IC 50 values in a range of 2-11 μM). Additionally, compound 3b has emerged from this study as the most active compound in the series against T. b. brucei with a MEC value of 12 μM. These three compounds are worth of further in vivo evaluation.
- Audisio, Davide,Messaoudi, Samir,Cojean, Sandrine,Peyrat, Jean-Fran?ois,Brion, Jean-Daniel,Bories, Christian,Huteau, Fran?oise,Loiseau, Philippe M.,Alami, Mouad
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scheme or table
p. 44 - 50
(2012/07/16)
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- FUSED PYRIDINE DERIVATIVES
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Fused pyridine derivatives shown as the general formula (I), and their pharmaceutically acceptable salts, stereoisomers or solvates thereof are disclosed, which belong to the technical field of medicines. The R1, R2, R3, Q, X and Y substituents in formula (I) are defined as in the description. Also disclosed are the preparation methods, pharmaceutical compositions comprising the compounds and uses of the compounds in the manufacture of the medicine for the treatment and/or prevention of noninsulin-dependent diabetes, hyperglycemia, hyperlipidemia and insulin resistance.
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Page/Page column 42
(2012/12/13)
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- FUSED PYRIDINE DERIVATIVES
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Fused pyridine derivatives shown as the general formula (I), and their pharmaceutically acceptable salts, stereoisomers or solvates thereof are disclosed, which belong to the technical field of medicines. The R1, R2, R3, Q, X and Y substituents in formula (I) are defined as in the description. Also disclosed are the preparation methods, pharmaceutical compositions comprising the compounds and uses of the compounds in the manufacture of the medicine for the treatment and/or prevention of noninsulin-dependent diabetes, hyperglycemia, hyperlipidemia and insulin resistance.
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(2012/12/13)
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- Discovery and biological activity of 6BrCaQ as an inhibitor of the Hsp90 protein folding machinery
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Heat shock protein90 (Hsp90) is a significant target in the development of rational cancer therapy, due to its role at the crossroads of multiple signaling pathways associated with cell proliferation and viability. Here, a novel series of Hsp90 inhibitors containing a quinolein-2-one scaffold was synthesized and evaluated in cell proliferation assays. Results from these structure-activity relationships studies enabled identification of the simplified 3-aminoquinolein-2-one analogue 2b (6BrCaQ), which manifests micromolar activity against a panel of cancer cell lines. The molecular signature of Hsp90 inhibition was assessed by depletion of standard known Hsp90 client proteins. Finally, processing and activation of caspases 7, 8, and 9, and the subsequent cleavage of PARP by 6BrCaQ, suggest stimulation of apoptosis through both extrinsic and intrinsic pathways. Hot stuff! A novel series of Hsp90 inhibitors containing a quinolein-2-one scaffold was synthesized and screened in cell proliferation assays. The most potent inhibitor, 6BrCaQ, exhibited strong antiproliferative activity against a panel of cancer cell lines and resulted in downregulation of Hsp90 client proteins. Moreover, 6BrCaQ induced a high level of apoptosis in MCF-7 breast cancer cells, and was found to mediate cell death in a p23-independent manner.
- Audisio, Davide,Messaoudi, Samir,Cegielkowski, Lukasz,Peyrat, Jean-Francois,Brion, Jean-Daniel,Methy-Gonnot, Delphine,Radanyi, Christine,Renoir, Jack-Michel,Alami, Mouad
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experimental part
p. 804 - 815
(2012/01/06)
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- Structure-activity relationships in human toll-like receptor 7-active imidazoquinoline analogues
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Engagement of toll-like receptors serve to link innate immune responses with adaptive immunity and can be exploited as powerful vaccine adjuvants for eliciting both primary and anamnestic immune responses. TLR7 agonists are highly immunostimulatory without inducing dominant proinflammatory cytokine responses. A structure-activity study was conducted on the TLR7-agonistic imidazoquinolines, starting with 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4, 5-c]quinolin-1-yl)-2-methylpropan-2-ol as a lead. Modifications of the secondary amine of the C2 ethylaminomethylene side chain are poorly tolerated. The 4-amino group must be retained for activity. Replacement of the imidazole ring of the scaffold with triazole or cyclic urea led to complete loss of activity. A systematic exploration of N1-benzyl-C2-alkyl substituents showed a very distinct relationship between alkyl length and TLR7-agonistic potency with the optimal compound bearing a C2-n-butyl group. Transposition of the N 1 and C2 substituents led to the identification of an extremely active TLR7-agonistic compound with an EC50 value of 8.6 nM. The relative potencies in human TLR7-based primary reporter gene assays were paralleled by interferon-α induction activities in whole human blood models.
- Shukla, Nikunj M.,Malladi, Subbalakshmi S.,Mutz, Cole A.,Balakrishna, Rajalakshmi,David, Sunil A.
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experimental part
p. 4450 - 4465
(2010/08/20)
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- METHODS FOR THE PREPARATION OF IMIDAZOLE-CONTAINING COMPOUNDS
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The present invention generally relates to methods for the preparation of compounds that contain imidazole moieties. In some embodiments, the methods include the reaction of a diamine with a dichloroimmonium compound to produce the imidazole moiety. In some embodiments, the methods are employed to prepare compounds having the Formulas II, II or III below: I II III wherein the constituent variables are as described herein.
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Page/Page column 110
(2008/06/13)
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- 4-Aryl-thio-pyridin-2(1H)-ones, medicines containing them and their uses in the treatment of illnesses linked to HIV
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PCT No. PCT/FR96/01204 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Jul. 30, 1996 PCT Pub. No. WO97/05113 PCT Pub. Date Feb. 13, 1997Compounds of formula (3) in which: R1 and R2 independently represent an atom of hydrogen, an aliphatic group or an alkyloxyalkyl group in which the alkyl chains are from C1 to C4 or together form an aromatic ring; R3 represents: an atom of hydrogen, or an NHR5 group in which R5 represents an atom of hydrogen or a COR6 group in which R6 is an aliphatic or aromatic group, or an NO2 group or a COOR7 group in which R7 is an aliphatic group, R4 represents a phenyl or heterocyclic group. These compounds can be used in the treatment of illnesses linked to the HIV virus.
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- 1H-imidazo?4,5-c!quinolin-4-amines
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Novel 1H-imidazo?4,5-c!quinolin-4-amines are disclosed. The compounds function as antiviral agents and they are potential synthetic intermediates in the preparation of known antiviral agents and labeled known antiviral agents. Processes for the preparation of the compounds, methods for their antiviral use, and methods of inducing interferon biosynthesis, are also described.
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- 4-hydroxy-3-nitro-1,2-dihydroquinolin-2-ones and the use thereof as excitatory amino acid and glycine receptor antagonists
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Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer''s disease, amyotrophic lateral sclerosis, Huntington''s disease and
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- A new series of pyridinone derivatives as potent non-nucleoside human immunodeficiency virus type 1 specific reverse transcriptase inhibitors
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4-(Arylthio)-pyridin-2(1H)-ones variously substituted in their 3-, 5-, and 6-positions have been synthesized as a new series of 1-[(2- hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)-pyridinone hybrid molecules. Biological studies revealed that some of them show potent HIV-1 specific reverse transcriptase inhibitory properties. Compounds 16 and 7c, the most active ones, inhibit the replication of HIV-1 at 3 and 6 nM, respectively.
- Dolle,Fan,Chi Hung Nguyen,Aubertin,Kirn,Andreola,Jamieson,Tarrago-Litvak,Bisagni
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p. 4679 - 4686
(2007/10/03)
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- 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines
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A process for the preparation of 1-substituted, 4-substituted-1H-imidazo[4,5-c]quinolines, intermediates in the preparation of such compounds, and processes for the preparation of such intermediates.
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- Anti-allergenic carbostyril derivatives
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A class of 4-hydroxy-3-nitroearbostyril derivatives are useful in the inhibition of certain types of antigen antibody reactions.
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