TW201943717A - FMS-like tyrosine kinase inhibitors - Google Patents

Abstract

The present invention relates to Fms-like tyrosine kinase (FLT3) inhibitors. The present invention provides novel 4-quinolinone derivatives used as FLT3 inhibitors and for treatment and/or prevention of tumors.

Description

FMS tyrosine kinase inhibitors

The present invention relates to Fms-like tyrosine kinase (FLT3) inhibitors. The present invention provides novel 4-quinolinone derivatives for use as FLT3 inhibitors and for treating and / or preventing tumors.

FLT3 is a class III receptor tyrosine kinase (RTK) related to the receptor structure of platelet-derived growth factor (PDGF), community stimulating factor 1 (CSF1), and KIT ligand (KL); these RTKs contain extracellular regions Among the five immunoglobulin-like domains and the intracellular tyrosine kinase domain, which are divided into two parts by a specific hydrophilic insertion (kinase insertion). FLT3 plays an important role in hematopoiesis. Members of this subgroup of the family include FLT3, platelet-derived growth factor receptors (PDGFR-α and PDGFR-β) and are characterized by an extracellular domain consisting of five immunoglobulin-like (Ig-like) domains, a single span The membrane region, the cytoplasmic near-membrane domain (JM), and the cytoplasmic tyrosine kinase domain are interrupted by the kinase inert domain (KID). Two groups independently reported selection of the FLT3 gene. FLT3 is also found in the placenta, gonads, and brain and is highly expressed in a variety of hematopoietic malignancies, including 70-100% of acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), and chronic myelogenous leukemia. which performed. Several FLT3 inhibitors (such as PKC412 (N-benzylidene astrosporin) (Blood. January 1, 2006; 107 (1): 293-300. Epub September 2005) and SU5614 (Haematologica. November 2005; 90 (11): 1577-8)) has been shown to have antitumor activity. However, the industry continues to need to develop anti-tumor drugs.

The present invention relates to substituted 4-quinolinone derivatives that are useful as FLT3 inhibitors and for the treatment and / or prevention of tumors. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs, and this term is used in this context to illustrate the invention. The terms used in the description are only used to explain specific embodiments, and are not intended to limit the present invention. If a range of values is provided, it should be understood that each intermediate value between the upper and lower limits of the range (to the tenth of the lower limit unit unless the context clearly indicates otherwise) (e.g. In the case of a group, in this case, providing the number of each carbon atom in the range) and any other stated or intermediate value in the range is encompassed by the present invention. The upper and lower limits of these smaller ranges may be independently included in the smaller ranges and also encompassed by the invention, subject to any explicitly excluded limits within the stated ranges. If the stated range includes one or both of the limits, ranges excluding both of those included limits are also included in the invention. Unless the context clearly indicates otherwise, as used herein and in the scope of the accompanying patent application, the article "a (a and an)" means one or more of the grammatical recipients of that article (i.e., means at least One). For example, "element" means one element or more than one element. As used herein in the description and the scope of the patent application, the phrase "and / or" should be understood to mean "either or both" of the elements so combined, that is, in some cases, in a combined manner and in Elements that exist separately in other cases. Multiple elements listed with "and / or" shall be considered to be the same, that is, "one or more" of the elements so combined. Depending on the circumstances, there are elements other than those specifically identified by the "and / or" clause, whether related or unrelated to those elements of the specific identification. The terms "halo" and "halogen" as used herein refer to an atom selected from the group consisting of fluorine, chlorine, bromine and iodine. The term "alkyl" refers to a straight or branched hydrocarbon chain group consisting of only carbon and hydrogen atoms, free of unsaturation, and having 1 to 15 carbon atoms (e.g. C₁ -C₁₅ alkyl). In certain embodiments, the alkyl group contains 1 to 13 carbon atoms (e.g., C₁ -C₁₃ alkyl). In certain embodiments, the alkyl group contains 1 to 8 carbon atoms (e.g., C₁ -C₈ alkyl). In other embodiments, the alkyl group contains 1 to 5 carbon atoms (e.g., C₁ -C₅ alkyl). In other embodiments, the alkyl group contains 1 to 4 carbon atoms (e.g., C₁ -C₄ alkyl). In other embodiments, the alkyl group contains 1 to 3 carbon atoms (e.g., C₁ -C₃ alkyl). In other embodiments, the alkyl group contains 1 to 2 carbon atoms (e.g., C₁ -C₂ alkyl). In other embodiments, the alkyl group contains one carbon atom (e.g., C₁ alkyl). In other embodiments, the alkyl group contains 5 to 15 carbon atoms (e.g., C₅ -C₁₅ alkyl). In other embodiments, the alkyl group contains 5 to 8 carbon atoms (e.g., C₅ -C₈ alkyl). In other embodiments, the alkyl group contains 2 to 5 carbon atoms (e.g., C₂ -C₅ alkyl). In other embodiments, the alkyl group contains 3 to 5 carbon atoms (e.g., C₃ -C₅ alkyl). In other embodiments, the alkyl group is selected from the group consisting of methyl, ethyl, 1-propyl (n-propyl), 1-methylethyl (isopropyl), 1-butyl (n-butyl), 1 -Methylpropyl (second butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (third butyl), 1-pentyl (n-pentyl). The alkyl group is attached to the rest of the molecule by a single bond. Unless stated otherwise specifically in the specification, an alkyl group is optionally substituted with one or more substituents. The term "alkenyl" as used herein denotes a monovalent group derived from a hydrocarbon moiety containing 2 to 6 or 2 to 8 carbon atoms and having at least one carbon-carbon double bond in certain embodiments. The double bond may or may not be the point of attachment to another group. Alkenyl includes, but is not limited to, for example, vinyl, propenyl, butenyl, 1-methyl-2-buten-1-yl, heptenyl, octenyl, and the like. The term "alkoxy" refers to a group bonded via an oxygen atom of the formula -O-alkyl, where alkyl is an alkyl chain as defined above. The term "alkenyl" refers to a straight or branched hydrocarbon chain group consisting of only carbon and hydrogen atoms, containing at least one carbon-carbon double bond, and having 2 to 12 carbon atoms. In certain embodiments, alkenyl contains 2 to 8 carbon atoms. In other embodiments, alkenyl contains 2 to 4 carbon atoms. Alkenyl is attached to the rest of the molecule by a single bond, such as ethenyl (i.e. vinyl), prop-1-enyl (i.e. allyl), but-1-enyl , Pent-1-enyl, pent-1,4-dienyl and the like. Unless stated otherwise specifically in the specification, alkenyl is optionally substituted with one or more substituents. The term "cycloalkyl" as used herein denotes a monovalent group derived from a monocyclic or polycyclic saturated or partially unsaturated carbocyclic compound. C₃ -C₈ -Examples of cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentyl, and cyclooctyl. The term "aryl" as used herein refers to a monocyclic or polycyclic carbocyclic ring system having one or more fused or non-fused aromatic rings, including but not limited to phenyl, naphthyl, tetrahydronaphthyl, di Hydroindenyl, indenyl and the like. The term "heteroaryl" as used herein refers to a monocyclic or polycyclic (e.g., bicyclic or tricyclic or more) fused or non-fused group or ring system having at least one aromatic ring, having 5 Up to 10 ring atoms, one of which is an additional heteroatom independently selected from S, O and N; 0, 1 or 2 ring atoms are independently selected from S, O and N; and the remaining ring atoms are carbon. Heteroaryl groups include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , Thienyl, furyl, quinolinyl, isoquinolinyl, benzimidazolyl, benzoxazolyl, quinazoline, and the like. The term "heterocycloalkyl" as used herein refers to a non-aromatic 3-membered ring, 4-membered ring, 5-membered ring, 6-membered ring, or 7-membered ring, or a bicyclic or tricyclic group fused or non-fused system Where (i) at least one ring contains between 1 and 3 heteroatoms independently selected from oxygen, sulfur and nitrogen, (ii) each 5-membered ring has 0 to 1 double bond and each 6 Member ring with 0 to 2 double bonds, (iii) nitrogen and sulfur heteroatoms may be oxidized as appropriate, (iv) nitrogen heteroatoms may be quaternized as appropriate, and (iv) any of the rings may be dense Combined to the benzene ring. Representative heterocycloalkyls include, but are not limited to, [1,3] dioxolane, pyrrolidinyl, pyrazolinyl, pyrazolyl, imidazolinyl, imidazolyl, hexahydropyridyl, hexahydropyridyl Hydropyrazinyl, oxazolyl, isoxazolyl, morpholinyl, thiazolyl, isothiazolyl, and tetrahydrofuranyl. The term "pharmaceutically acceptable salt" refers to a salt prepared from a pharmaceutically revealable non-toxic base or acid including inorganic or organic bases and inorganic or organic acids. Salts of basic compounds encompassed by the term "pharmaceutically acceptable salts" refer to non-toxic salts of the compounds of the present invention which are generally prepared by reacting a free base with a suitable organic or inorganic acid. Representative salts of the basic compounds of the present invention include, but are not limited to, the following salts: acetate, ascorbate, adipate, alginate, aspartate, benzenesulfonate, benzoate, carbonate Hydrogen salt, hydrogen sulfate, tartrate, borate, bromide, butyrate, camphor salt, camphor sulfonate, d-camphorsulfonate, carbonate, chloride, clavulanate , Citrate, cyclopentanepropionate, diethylacetic acid, digluconate, dihydrochloride, dodecyl sulfate, edetate, ethanedisulfonate, etolate ), Ethanesulfonate, ethanesulfonate, formate, fumarate, gluceptate (glucoheptanoate), gluconate, glutamate, glycerol phosphate, para-α-hydroxyl Glycolyllarsanilate, hemisulfate, heptanoate, hexanoate, hexyl resorcinol, hydrabamate, bromide, chloride, 2-hydroxyethane Sulfonate, hydroxynaphthoate, iodide, isonicotinate, isothiosulfate, lactate, lactate, month Laurate, malate, maleate, mandelate, mesylate, methyl nitrate, methyl sulfate, methane sulfonate, mucate, 2-naphthalene sulfonate, naphthalene sulfonate Acid salt, nicotinate, nitrate, oleate, oxalate, pamoate (paraben), palmitate, pantothenate, pectate, persulfate , Phosphate / hydrogen phosphate, pimelate, phenylpropionate, polygalacturonate, Propionate, salicylate, stearate, sulfate, hypoacetate, succinate, tannate, tartrate, theophylline, thiocyanate, tosylate, triethyliodide , Trifluoroacetate, undecanoate, valerate and the like. In addition, if the compounds of the present invention have an acidic moiety, suitable pharmaceutically acceptable salts include (but are not limited to) salts derived from inorganic bases, including aluminum, ammonium, calcium, copper, iron, Iron, lithium, magnesium, manganese, manganese, potassium, sodium, zinc, and the like. Salts derived from pharmaceutically acceptable organic non-toxic bases include the following salts: primary, secondary, and tertiary amines, cyclic amines, dicyclohexylamine, and basic ion exchange resins, such as arginine, betaine , Caffeine, choline, N, N-dibenzylethylenediamine, diethylamine, 2-diethylaminoethanol, 2-dimethylaminoethanol, ethanolamine, ethylamine, ethylenediamine, N-ethyl Morpholine, N-ethylhexahydropyridine, reduced glucosamine, glucosamine, histidine, harmine, isopropylamine, lysine, methyl-reduced glucosamine, morpholine, hexahydropyrazine, six Hydropyridine, polyamine resin, procaine, purine, theobromine, triethylamine, trimethylamine, tripropylamine, tromethamine, and the like. Also included are basic nitrogen-containing groups that can be quaternized with reagents such as: lower alkyl halides such as methyl, ethyl, propyl and butyl chlorides, bromides and iodides; Alkyl esters, such as dimethyl sulfate, diethyl sulfate, dibutyl sulfate, and dipentyl sulfate; long-chain halides, such as decyl, lauryl, myristyl, and stearyl. Chlorides, bromides and iodides; aralkyl halides, such as benzyl and phenethyl bromides, and others. The term "individual" includes living organisms such as humans, monkeys, cows, sheep, horses, pigs, cows, goats, dogs, cats, mice, rats, cultured cells and their transgenic species. In the preferred embodiment, each system is human. The term "administration" includes an administration route which allows the active ingredient of the present invention to perform its intended function. The term "treat or treatment" refers to a method of reducing the effect of a disease or condition. Treatment can also refer to a method that reduces the underlying disease of the disease or condition itself and is therefore not merely a symptom. Treatment may be any reduction from a natural level and may be, but is not limited to, a complete elimination of a disease, condition, or symptom of a disease or condition. The term "prevent, prevent or prevent" means to inhibit or prevent symptoms related to the target disease. The phrase "therapeutically effective amount" refers to the amount of a compound, material, or composition comprising a compound of the invention that is effective to produce the desired therapeutic effect at a reasonable benefit / risk ratio applicable to any medical treatment. In one aspect, the present invention provides a compound having the following formula (I-1), (I-2), (I-3) or (I-4),or, Where Y is [P] n, where P is -CH-, -N-, or -O-; X is [Q] n, where Q is -CH₂ -, -NH-, -O-, -S-, -SO₂ -Or -N-alkyl; n is 0 or 1; R₁ Represents mono-, di-, tri- or tetra substitution and is selected from the group consisting of halogen, -OH, -NH₂ , -NO₂ , -CN, alkyl, alkenyl, haloalkyl, -NHR_a , N (R_b )₂ , -OR_a , 3-membered cycloalkyl, 4-membered cycloalkyl, 5-membered cycloalkyl or 6-membered cycloalkyl, 3-, 4-, 5- or 5- or 5-membered heteroatoms selected from N, O, and S 6-heterocycloalkyl, aryl or heteroaryl; R_a System H, alkyl, alkenyl, halogen, hydroxyalkyl, -OH, -NO₂ Or phenyl; R_b Alkyl, alkenyl or halogen; R₂ Department -NR_d R_e -, -O-alkyl, -C (= O)-5 or 6-membered aryl or -C (= O)-5 or 6-membered heteroaryl; R_d OH, alkyl, alkenyl, aryl, heteroaryl, heteroalkenyl, -alkylene-NR_a R_e , -Extended alkyl-N (R_b )₂ , -Extended alkyl-OR_c , -Alkylene-5 or 6-membered aryl, -alkylene-5 or 6-membered heteroaryl or 5 or 6-membered heterocycloalkyl or heteroaryl containing at least one N; R_e H, alkyl, alkenyl or aryl; or R_d R_e Forms a 3 to 8 membered heterocycloalkyl or heteroaryl ring with N, optionally via C₁ -C₃ Alkyl, C₁ -C₃ Alkylene-phenyl, third butyloxycarbonyl substituted or N substituted, R_c H, alkyl, alkenyl, halogen or phenyl; R₃ H, alkyl, alkenyl, halogen or CN, NH₂ Or NO₂ . Wherein the alkyl or alkenyl is unbranched or branched, unsubstituted or substituted with halogen, hydroxyl, amine or nitro; and where the cycloalkyl or heterocycloalkyl is unsubstituted or substituted with halogen, -OH , -NH₂ , -NO₂ , -CN, alkyl, alkenyl, -NHR_a , N (R_b )₂ Or -OR_a Substitution; conditions are when P is -CH- and n is 1, R at position 8₁ Not Cl; or a solvate, prodrug, stereoisomer, mirror isomer, or pharmaceutically acceptable salt thereof. In one embodiment, Q is -S- and n is 1. In one embodiment, P is -C- or -N- and n is 1. In one embodiment, R₁ CN, F, Cl, -OC_1-4 Alkyl, C_1-4 Alkyl or halo C_1-4 alkyl. In another embodiment, when P is -C-, Cl is bonded to C11, C10, C9 or C8; and when P is -C-, -OC_1-4 Alkyl, F, CN, -OC_1-4 Alkyl, C_1-4 Alkyl or halo C_1-4 The alkyl group is bonded to C10. In one embodiment, R₂ Department-NH-C_1-3 Alkylene-NHR_a , -NH-C_1-3 Alkylene-NH₂ , -NH-C_1-3 Alkyl-OH, -NH-C_1-3 Alkylene-NHC_1-4 Alkyl OH, -C_1-3 Alkylene-5 or 6-membered aryl, -C_1-3 Alkyl-5 or 6-membered heteroaryl. In another embodiment, R_a Department H; Rc is hydroxyl C_1-4 alkyl. In one embodiment, R₃ For hydrogen. In some embodiments, the compounds of the invention are selected from the group consisting of: The invention encompasses all stereoisomeric forms of the compounds of formulae (I-1), (I-2), (I-3) and (I-4). The asymmetric centers existing in the compounds of the formulae (I-1), (I-2), (I-3) and (I-4) may all have the (R) configuration or the (S) configuration independently of each other. When the bond to a chiral carbon is shown as a straight line in the structural formula of the present invention, it should be understood that the (R) and (S) configurations of the chiral carbon and therefore the two mirror image isomers and mixtures thereof are covered . This mirror image isomer ((R) or (S), at the center) is expected when drawing a particular configuration. Similarly, when enumerating the names of compounds without the chiral name of the chiral carbon, it should be understood that the name covers the chiral carbon (R) and (S) configurations and therefore individual mirror image isomers and mixtures thereof. The invention includes all possible enantiomers, regioisomers, and non-enantiomers, and mixtures of two or more stereoisomers, such as all of the enantiomers and / or non-enantiomers A mixture of ratios. Therefore, mirror isomers are the subject of the present invention and are in the form of mirror isomers (both left and right isomers), in the form of racemates, and in all ratios of the two mirror isomers. Of mixtures. In the case of cis / trans isomerism, the invention includes cis and trans forms and mixtures of all ratios of those forms. If desired, the preparation of individual stereoisomers can be carried out by separating the mixture by common methods, such as by chromatography or crystallization, by synthesizing using stereochemically homogeneous starting materials, or by stereoselective synthesis. Optionally, derivatization can be performed before separation of stereoisomers. The separation of a mixture of stereoisomers can be carried out in an intermediate step during the synthesis of compounds of formulae (I-1), (I-2), (I-3) and (I-4) or they can be used for the final racemic product get on. Absolute stereochemistry can be determined by X-ray crystallography of the crystalline product or crystalline intermediate (derived with a reagent containing a stereocenter of a known configuration if necessary). If the compounds of the present invention can be tautomeric, all individual tautomers and mixtures thereof are included in the scope of the present invention. The present invention includes all such isomers, as well as the salts, solvates (including hydrates), and solvates of the racemates, mirror isomers, non-image isomers, and tautomers and mixtures thereof. salt. As used herein, regardless of whether specific abbreviations are specifically defined, the symbols and conventions used in such processes, schemes, and examples should be consistent with those used in the current scientific literature, for example, the Journal of the American Chemical Society or the Journal of Biological Chemistry. In particular, but not limited to, the following abbreviations may be used in the examples and throughout the specification: g (gram); mg (mg); mL (ml); μL (microliter); mM (millimolar concentration); M (micromolar) Ear concentration); Hz (Hertz); MHz (Megahertz); mmol (millimolar); hr or hrs (hour); min (minute); MS (mass spectrometry); ESI (electrospray ionization); TLC (thin Layer chromatography); and HPLC (high pressure liquid chromatography). For all of the following examples, standard processing and purification methods known to those skilled in the art can be used. Unless otherwise indicated, all temperatures are expressed in ° C (Celsius). Unless otherwise stated, all reactions are performed at room temperature. The synthetic methods explained herein are intended to illustrate applicable chemical methods by using specific examples, and do not indicate the scope of this disclosure. The compounds of the formula (I-1), (I-2), (I-3) and (I-4) according to the present invention are prepared according to a general chemical synthesis procedure. The preparation of examples of the compounds of the invention is described below. Suitable synthesis of the compounds of the invention can be found in the examples below. In another aspect, the present invention provides a pharmaceutical composition comprising a compound of any one of Formulae I-I to I-4 or a pharmaceutically acceptable ester, salt or prodrug thereof, and a pharmaceutically acceptable carrier. To prepare the pharmaceutical composition of the present invention, one or more of the compounds of the present invention as an active ingredient is thoroughly mixed with a pharmaceutical carrier according to conventional pharmaceutical mixing techniques, which is administered end-view (e.g., orally or parenterally (e.g., muscle) Inside)) Many forms are used as the desired formulation form. In preparing the composition in an oral dosage form, any commonly used pharmaceutical medium may be used. Thus, for liquid oral preparations (e.g., suspensions, elixirs, and solutions), suitable carriers and additives include water, glycols, oils, alcohols, flavoring agents, preservatives, colorants, and the like; for solid oral preparations (e.g., Powder, capsule, film-coated tablet, gelatin capsule and lozenge), suitable carriers and additives include starch, sugar, diluent, granulating agent, lubricant, binder, disintegrant and the like. Because tablets and capsules are easy to administer, they represent the most advantageous form of oral dosage unit, in which case solid pharmaceutical carriers are clearly employed. If desired, the lozenges may be sugar coated or enteric coated by standard techniques. For parenteral administration, the carrier usually contains sterile water, but may include other ingredients, for example, for purposes such as to aid dissolution or for preservation. Injectable suspensions may also be prepared, in which case suitable liquid carriers, suspensions and the like may be employed. The pharmaceutical compositions herein will contain each dosage unit (e.g., lozenges, capsules, powders, injections, teaspoons, and the like) in an amount necessary to deliver an effective dose as described above. The novel compositions that can be incorporated into the present invention are in liquid form for oral administration or by injection, including aqueous solutions, suitably flavored syrups, aqueous or oily suspensions, and the use of edible oils such as cottonseed oil, sesame oil, coconut oil, or peanut oil ) Flavored emulsions and tinctures and similar pharmaceutical vehicles. Dispersants or suspending agents suitable for aqueous suspensions include synthetic and natural gums such as tragacanth, gum arabic, alginate, dextran, sodium carboxymethylcellulose, methylcellulose, polyvinylpyrrolidine Ketone or gelatin. Oral tablets and capsules are usually supplied in unit dosage form and contain conventional excipients such as binders, fillers (including cellulose, mannitol, lactose), diluents, lozenges, lubricants (including hard Magnesium stearate), detergents, disintegrating agents (such as polyvinyl pyrrolidone and starch derivatives such as sodium starch glycolate), colorants, flavoring agents, and wetting agents (such as sodium lauryl sulfate). Oral solid compositions can be prepared by conventional blending, filling or tableting methods. The blending operation may be repeated to distribute the active ingredient throughout the composition containing a large amount of filler. These operations are customary. For parenteral administration, fluid unit doses containing the compound and a sterile vehicle can be prepared. Depending on the vehicle and concentration, the compound can be suspended or dissolved. Parenteral solutions are usually prepared by dissolving the compound in a vehicle, sterilizing by filtration, filling a suitable vial, and sealing. Advantageously, adjuvants such as local anesthetics, preservatives and buffering agents can also be dissolved in the vehicle. To increase stability, the composition can be frozen after filling the vial and the water can be removed under vacuum. Parenteral suspensions are prepared in substantially the same manner, except that the compound can be suspended in the vehicle rather than dissolved, and sterilized by exposure to ethylene oxide before being suspended in a sterile vehicle. Advantageously, a surfactant or wetting agent may be included in the composition to facilitate uniform distribution of the compounds of the present application. Pharmaceutical preparations for administration by inhalation can be delivered from an insufflator or nebulizer pressurized pack. In another aspect, the invention provides a method of inhibiting FLT3, comprising contacting a cell with a compound of the invention. In another aspect, the invention provides a method of treating or preventing a disease associated with FLT3 inhibition in an individual, comprising administering an effective amount of a compound of the invention. The compounds of the invention are useful in the treatment or prevention of any disease and / or condition in which FLT3 inhibition is desired. Inhibition of enzymes will result in reduced tumor growth. Therefore, the present invention provides a method for treating or preventing a tumor or cancer. Examples of cancers that can be treated according to the present teachings include, but are not limited to, invasive breast cancer, adenocarcinoma, lung cancer (non-small cell, squamous cell carcinoma, adenocarcinoma and large cell lung cancer), liver cancer, colorectal cancer, brain cancer, Head and neck cancer (e.g. nerve / glioblastoma), breast cancer, ovarian cancer, bladder transitional cell cancer, prostate cancer, oral squamous cell carcinoma, osteosarcoma, adrenal cortex cancer, gastrointestinal tumors (including colorectal cancer), biliary tract Cancer (e.g., gallbladder cancer (GBC)), bladder cancer, esophageal cancer, gastric cancer, cervical cancer, salivary gland cancer, diarrhea, benign neoplasm, ductal carcinoma in situ, paronychia, bile duct cancer, kidney cancer, pancreatic cancer, Myeloblastoma, glioblastoma; breast duct, HER2-positive and triple-negative breast tumors; hematological malignancies and leukemia (acute myeloid leukemia (AML), B-precursor acute lymphoblastic leukemia (ALL) ), A small portion of T cell ALL and chronic myelogenous leukemia (CML)). The compound or a pharmaceutically acceptable salt thereof is oral, nasal, transdermal, pulmonary, inhalation, buccal, sublingual, intraperitoneal, subcutaneous, intramuscular, intravenous, rectal, intrapleural, intrathecal and Parenteral administration. In one embodiment, the compound is administered orally. Those skilled in the art will recognize the advantages of certain routes of administration. The dosage regimen of the compound is selected based on a variety of factors, including the type, species, age, weight, sex, and medical condition of the patient; the severity of the condition to be treated; the route of administration; the kidney and liver function of the patient; A specific compound or a salt thereof. A skilled physician or veterinarian can easily determine and prescribe the effective amount of the drug required to prevent, counteract or prevent the progress of the condition. Now that the present invention has been described with the help of written description, those skilled in the art will recognize that the present invention can be practiced in various embodiments and the following descriptions and examples are used for illustrative purposes, without limiting the scope of the following patent applications.Examples All key raw materials were purchased from various commercial sources and used without further purification. Some key raw materials and reagents are available internally. Using DMSO-d on a 400 MHz NMR spectrometer₆ CDCl₃ Or TFA-d₁ Recorded as deuterated solvent¹ H NMR spectrum. According to the followingmethod AK One of them performed LC-MS analysis of the compound.method A Column: Symmetry- C18 4.6 × 75 mm, 3.5 µm; Wavelength: 254 nm; Flow rate: 0.8 mL / min; Run time: 12 minutes; Time and mobile phase gradient (time (min) / B): 0/50 , 3/95, 9/95, 10/50, 12/50 [B: acetonitrile; A: ammonium formate (20 millimolar concentration in water)]; LC- Agilent technologies-1260 Infinity II series; MASS: Agilent technologies-6120 Quadrupole LC / MS-API-ESI.method B Column: Symmetry- C18 4.6 × 75 mm, 3.5 µm; Wavelength: 254 nm; Flow rate: 0.8 mL / min; Run time: 10 minutes; Time and mobile phase gradient (time (min) / B): 0/5 , 2/95, 7/95, 7.1 / 5, 10/5 [B: acetonitrile; A: 0.1% formic acid in water]; LC- Agilent technologies-1260 Infinity II series; MASS: Agilent technologies-6120 Quadrupole LC / MS-API-ESI.method C Column: Symmetry- C18 4.6 × 75 mm, 3.5 µm; Wavelength: 254 nm; Flow rate: 0.8 mL / min; Run time: 12 minutes; Time and mobile phase gradient (time (min) / B): 0/50 , 3/95, 9/95, 10/50, 12/50 [B: acetonitrile; A: ammonium formate (10 millimolar concentration in water)]; LC- Agilent technologies-1260 Infinity II series; MASS: Agilent technologies-6120 Quadrupole LC / MS-API-ESI.method D Column: Agilent poroshell 120 EC- C18 3.0 × 50 mm, 2.7 µm; Wavelength: 254 nm; Flow rate: 0.8 mL / min; Run time: 12 minutes; Time and mobile phase gradient (time (min) / B): 0/50, 3/95, 9/95, 10/50, 12/50 [B: acetonitrile; A: ammonium formate (20 mmol in water)]; LC- Agilent technologies-1260 Infinity II series; MASS: Agilent technologies-6120 Quadrupole LC / MS-API-ESI.method E Column:-Agilent poroshell 120 EC- C18 4.6 × 100 mm, 2.7µm; Wavelength: 254 nm; Flow rate: 0.8 mL / min; Run time: 12 minutes; Time and mobile phase gradient (time (min) / B) : 0/50, 3/95, 9/95, 10/50, 12/50 [B: acetonitrile; A: ammonium formate (20 millimolar concentration in water)]; LC- Agilent technologies-1260 Infinity II series ; MASS: Agilent technologies-6120 Quadrupole LC / MS-API-ESI.method F Agilent poroshell 120 EC- C18 4.6 × 100 mm, 2.7µm; wavelength: 254 nm; flow rate: 0.8 mL / min; running time: 10 minutes; time and mobile phase gradient (time (min) / B): 0/10 , 3/80, 7/80, 7.01 / 10, 10/10 [B: acetonitrile; A: ammonium formate (20 millimolar concentration in water)]; LC- Agilent technologies-1260 Infinity II series; MASS: Agilent technologies-6120 Quadrupole LC / MS-API-ESI.method G Agilent poroshell 120 EC- C18 4.6 × 100 mm, 2.7µm; Wavelength: 254 nm; Flow rate: 0.8 mL / min; Run time: 12 minutes; Time and mobile phase gradient (time (min) / B): 0/20 , 3/90, 10/90, 10.1 / 20, 12/20 [B: acetonitrile; A: ammonium formate (20 millimolar concentration in water)]; LC- Agilent technologies-1260 Infinity II series; MASS: Agilent technologies-6120 Quadrupole LC / MS-API-ESI.method H Agilent poroshell 120 EC- C18 4.6 × 100 mm, 2.7µm; wavelength: 254 nm; flow rate: 0.8 mL / min; running time: 10 minutes; time and mobile phase gradient (time (min) / B): 0/5 , 2/95, 7/95, 7.1 / 5, 10/5 [B: acetonitrile; A: 0.1% formic acid in water]; LC- Agilent technologies-1260 Infinity II series; MASS: Agilent technologies-6120 Quadrupole LC / MS -API-ESI.method I Agilent poroshell 120 EC- C18 4.6 × 100 mm, 2.7µm; wavelength: 254 nm; flow rate: 0.8 mL / min; running time: 8 minutes; time and mobile phase gradient (time (min) / B): 0/20 , 2/90, 6/90, 6.5 / 20, 8/20 [B: acetonitrile; A: ammonium formate (20 millimolar concentration in water)]; LC- Agilent technologies-1260 Infinity II series; MASS: Agilent technologies-6120 Quadrupole LC / MS-API-ESI.method J : Column:-Agilent poroshell 120 EC- C18 4.6 × 100 mm, 2.7µm; wavelength: 254 nm; flow rate: 0.8 mL / min; run time: 12 minutes; time and mobile phase gradient (time (min) / B) : 0/50, 3/95, 9/95, 10/50, 12/50 [B: acetonitrile; A: ammonium formate (20 millimolar concentration in water)]; LC- Agilent technologies-1260 Infinity II series ; MASS: Agilent technologies-6120 Quadrupole LC / MS-API-ESI.method K : Column:-Symmetry- C18, 4.6 × 75 mm, 3.5µm; wavelength: 254 nm; flow rate: 0.8 mL / min; running time: 12 minutes; time and mobile phase gradient (time (min) / B): 0 / 50, 3/95, 9/95, 10/50, 12/50 [B: acetonitrile; A: ammonium formate (20 millimolar concentration in water)]; LC- Agilent technologies-1260 Infinity II series; MASS : Agilent technologies-6120 Quadrupole LC / MS-API-ESI. Preparation example General procedure A Step-1: Simultaneously add an aqueous solution of chloroacetic acid (1.1 equivalent) and an aqueous solution of NaOH [3.0 equivalent, dissolved in about 2 times the volume of water] to a solution of the corresponding substituted thiophenol (1.0 equivalent) in water, and the mixture Heat to 50 ° C and hold for 4-5 hours. After the completion of the reaction is monitored by TLC, the reaction mass is cooled to room temperature and slowly diluted with 5N HCl (pH about 4-5). The resulting suspension was filtered; washed with water and dried under vacuum to give an off-white solidseries 2 [Compound2a-2o ].General procedure B ; Step-2: Indigo (0.9 equivalent),series 2 A mixture of (1.0 equivalent) and sodium acetate (0.2 equivalent) in AcOH (4-5 volumes) was heated at 150 ° C for 24 hours. After cooling, the formed solid was suspended with acetic acid (10 times the volume); filtered and washed with acetic acid: water (1: 9) to remove unreacted isatin. The remaining solid was washed again with water and dried under vacuum to obtainseries 3 [Compound3a-3o ].General procedure C ; Step-3: Willseries 3 POCl₃ The solution in (3-4 volumes) was heated at 160 ° C for 48 hours. After cooling, the mixture was carefully poured into ice at 0 ° C. The separated precipitate obtained was collected by filtration. Suspend the filter cake in 10% NaHCO₃ The solution was stirred vigorously for 1 hour. Collect the resulting precipitate and use H₂ O washes. The crude solid was washed with an EtOAc: THF mixture (1: 1) and dried under vacuum to give the following scaffold compound.General procedure D :willseries 4 (1.0 equivalent), a mixture of amine (5.0 equivalent) in DMSO (approximately 4-5 times the volume) is heated in a flask at 120 ° C for 2-3 hours (note: when the target involves the use of amines with a bp <120 ° C) Next, the reaction is carried out in a sealed tube). After the completion of the reaction is monitored by TLC, the reaction mass is cooled to RT and quenched in water. The resulting precipitate was diluted with a 10% MeOH / DCM mixture and extracted. The separated aqueous layer was re-extracted with 10% MeOH / DCM. The combined organic extracts were washed with a saline solution;₂ SO₄ Dry and concentrate to give the crude compound. The crude mixture was recrystallized or by FCC using MeOH / DCM / aqueous solution NH₃ The mixture was purified to give the title compound as a pale yellow to yellow solid.General procedure E : Add dropwise to a stirred solution of amine (5.0 equivalents) in DMSO (about 5 times the volume) at 120 ° Cseries 4 (1.0 equivalent) suspension in DMSO (about 4-5 times the volume) and the mixture was heated at the same temperature for 2-3 hours. After the completion of the reaction is monitored by TLC, the reaction mass is cooled to RT and quenched in water. The resulting precipitate was diluted with a 10% MeOH / DCM mixture and extracted. The aqueous layer was separated and re-extracted with 10% MeOH / DCM. The combined organic extracts were washed with a saline solution;₂ SO₄ Dry and concentrate to give the crude compound. The crude mixture was subjected to FCC using MeOH / DCM / aqueous NH₃ The mixture was purified to give the title compound as a pale yellow to yellow solid.General procedure F :willseries 4 (1.0 equivalent), a mixture of 4-methoxybenzylamine (5.0 equivalent) in DMSO (about 4-5 times the volume) was heated at 120 ° C for 2-3 hours. After the completion of the reaction is monitored by TLC, the reaction mass is cooled to RT and quenched in water. The resulting precipitate was filtered; washed with water and dried in vacuo to give the crude product, which was purified by the FCC using a MeOH / DCM mixture to give a pale yellow to yellow solidseries 4 . TFA (about 10 times the volume) andseries 4 (1.0 equivalent) of the mixture was stirred at RT for 4-5 hours. After the completion of the reaction is monitored by TLC, for example, the reaction mass is concentrated on a rotary evaporator. The resulting residue was quenched with ice-cold water and the resulting solid was filtered. Suspend the filter cake in saturated NaHCO₃ The solution (pH about 8) and stirred for 30 minutes. The suspension was filtered; washed with water and dried under vacuum to give the title compound as a pale yellow to yellow solid.General procedure G : At RT, towards Na₂ CO₃ (3.0 equivalents), ethylene glycol (5.0 equivalents) were added to the stirred mixture in DMSO (about 4-5 times the volume)series 4 (1.0 equivalent), and the mixture was heated in a reaction flask at 120 ° C for 2-3 hours. After the completion of the reaction is monitored by TLC, the reaction mass is cooled to RT and quenched in water. The resulting precipitate was diluted with a 10% MeOH / DCM mixture and extracted. The separated aqueous layer was re-extracted with 10% MeOH / DCM. The combined organic extracts were washed with a saline solution;₂ SO₄ Dry and concentrate to give the crude compound. The crude mixture was crystallized or purified by FCC to give the title compound as a pale yellow to yellow solid.General procedure H : Under RT, toseries 4 (1.1 equivalent), CS₂ CO₃ (1.6 eq.), BINAP (0.1 eq.) In a degassed solution in NMP (5 ml), then Pd (OAc)₂ (0.05 equivalent) and the appropriate amine (1.0 equivalent), and the mixture was refluxed for 2 hours. After the reaction is complete (as monitored by TLC), the reaction mixture is cooled to RT and filtered through celite. The filtrate was diluted with water (30 ml) and extracted in 10% MeOH / DCM (3 x 30 ml). The combined organic extracts were washed with water (25 ml), followed by a saline solution (25 ml). Pass the organic layer over anhydrous Na₂ SO₄ Dried and concentrated to a residue, which was purified by FCC to give the title compound as a pale yellow to yellow solid.General procedure I : Compound (1.0 equivalent), K at RT₂ CO₃ (2.1 equivalents) To the stirred mixture in DMF (approximately 4-5 times the volume) was added iodoethane or chlorotoluene (1.5 equivalents), and the mixture was stirred at RT. After the completion of the reaction is monitored by TLC, the reaction material is quenched in water. The resulting suspension was diluted with a 10% MeOH / DCM mixture and extracted. The separated aqueous layer was re-extracted with 10% MeOH / DCM. The combined organic extracts were washed with a saline solution;₂ SO₄ Dry and concentrate to give the crude compound. The crude mixture was purified by FCC to give the title compound as a pale yellow to yellow solid.General procedure J : At RT, add series to a stirred mixture of TEA (10.0 equivalents) and ethylamine.HCl (10.0 equivalents) in DMSO (about 4-5 times the volume)4 (1.0 equivalent), and the mixture was heated in a sealed tube at 120 ° C for 2-3 hours. After the completion of the reaction is monitored by TLC, the reaction mass is cooled to RT and quenched in water. The resulting precipitate was diluted with EtOAc and extracted. The separated aqueous layer was re-extracted with EtOAc. The combined organic extracts were washed with a saline solution;₂ SO₄ Dry and concentrate to give the crude compound. The crude mixture was purified by FCC to give the title compound as a pale yellow to yellow solid.General procedure K : To a stirred mixture of CDI (1.5 equivalents) and benzoic acid analog (1.2 equivalents) in DMSO (approximately 4-5 times volume) at 70 ° C, add 6-amino derivative (1.0 equivalent) and the same Continue stirring at temperature for 30 minutes. The temperature was raised to 140 ° C and the reaction mixture was further stirred at the same temperature for 16 hours. After the completion of the reaction is monitored by TLC, the reaction mass is cooled to RT and extracted into water. The resulting precipitate was diluted with a 10% MeOH / DCM mixture and extracted. The separated aqueous layer was re-extracted with 10% MeOH / DCM. The combined organic extracts were washed with a saline solution;₂ SO₄ Dry and concentrate to give the crude compound. FCC with MeOH / DCM / aqueous NH₃ The crude mixture was purified from the mixture to give the target compound as a yellow solid.General procedure L : At RT, add to the stirring mixture of series 4 (1.0 equivalent) in chloroform (about 200 times the volume)m -CPBA (5.0 equivalents) and the mixture was stirred at RT for 16-20 hours. After completion of the reaction is monitored by TLC, the solvent is concentrated. The crude product was purified by FCC to obtain the target compound as a pale yellow solid5a . plan 1 Examples 1 6- chlorine -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (4a) : Starting from 4-chlorothiophenol, the general procedure A-C was followed in 3 steps. Yield: 46% over 3 steps. ES-MS [M + 1]⁺ : 331.8; t_R : 6.95 minutes (Method-A).Examples 2 10- chlorine -6-((4- Methoxybenzyl ) Amine ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7700) : Synthesized according to the general procedure -E. Yield: 300 mg (92%). ES-MS [M + 1]⁺ : 432.9; t_R : 6.31 minutes (Method-A),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.33 (d,J = 8.4 Hz, 1H), 8.36 (d,J = 2.4 Hz, 1H), 7.98 (d,J = 9.2 Hz, 1H), 7.87 (dd,J = 8.4, 2.4 Hz, 1H), 7.71 (m, 1H), 7.66 (d,J = 7.6 Hz, 1H), 7.59 (m, 1H), 7.39, 7.36 (m, 1H), 6.84 (d,J = 8.4 Hz, 2H), 4.70 (d,J = 5.6 Hz, 1H), 3.67 (s, 3H).Examples 3 6- Amine -10- chlorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7702) : Synthesized according to the general procedure -F. Yield: 195 mg (81%). ES-MS [M + 1]⁺ : 312.9; t_R : 4.29 minutes (Method-A);¹ HNMR (400 MHz, TFA-d):δ 9.48 (d,J = 8.4 Hz, 1H), 8.73 (s, 1H), 8.00-7.85 (m, 5H).Examples 4 10- chlorine -6- ( Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7703) : Synthesized according to the general procedure -D. Yield: 120 mg (75%). ES-MS [M + 1]⁺ : 355.0; t_R : 6.84 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.33 (d,J = 8.4 Hz, 1H), 8.37 (d,J = 2.0 Hz, 1H), 7.97 (d,J = 8.4 Hz, 1H), 7.87 (dd,J = 8.4, 2.0 Hz, 1H), 7.66 (d,J = 8.4 Hz, 1H), 7.57 (ddd,J = 8.4, 6.8, 1.2 Hz, 1H), 7.35 (ddd,J = 8.4, 6.8, 1.2 Hz, 1H), 7.12 (dd,J = 5.6, 4.8 Hz, 1H), 3.52 (q,J = 6.0 Hz, 2H), 1.70 (m, 2H), 0.95 (t,J = 7.2 Hz, 3H).Examples 5 6- (3- Aminopropylamino ) -10- chlorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7704) : Synthesized according to the general procedure -E. Yield: 295 mg (88%). ES-MS [M + 1]⁺ : 370.0; t_R : 2.52 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.34 (d,J = 8.4 Hz, 1H), 8.38 (d,J = 1.2 Hz, 1H), 7.98 (d,J = 8.8 Hz, 1H), 7.88 (dd,J = 8.4, 1.6 Hz, 1H), 7.69 (d,J = 8.0 Hz, 1H), 7.60 (dd,J = 8.4, 6.8, 1H), 7.35 (dd,J = 8.0, 7.2, 1H), 6.5 (brs, 2H), 3.66 (m, 2H), 2.83 (t,J = 6.8 Hz, 2H), 1.91 (t,J = 6.8 Hz, 2H).Examples 6 10- chlorine -6- (3- (2- Hydroxyethylamino ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7701) : Synthesized according to the general procedure -D. Yield: 328 mg (55%). ES-MS [M + 1]⁺ : 413.9; t_R : 2.89 minutes (Method-B);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.33 (d,J = 8.8 Hz, 1H), 8.36 (d,J = 2.0 Hz, 1H), 7.93 (d,J = 8.4 Hz, 1H), 7.88 (dd,J = 8.8, 2.0 Hz, 1H), 7.66 (d,J = 8.0 Hz, 1H), 7.58 (dd,J = 8.0, 7.2 Hz, 1H), 7.35 (t,J = 7.6, 1H), 4.57 (brs, 1H), 3.62 (t,J = 6.4, 2H), 3.55 (m, 2H), 2.71 (t,J = 6.0 Hz, 2H), 2.63 (t,J = 5.6 Hz, 2H), 1.82 (t,J = 6.0 Hz, 2H).Examples 7 10- chlorine -6- (2- Hydroxyethylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7717) : Synthesized according to the general procedure -D. Yield: 213 mg (58%). ES-MS [M + 1]⁺ : 356.9; t_R : 4.21 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.30 (d,J = 8.4 Hz, 1H), 8.32 (d,J = 2.4 Hz, 1H), 7.95 (d,J = 8.4 Hz, 1H), 7.84 (dd,J = 8.4, 2.0 Hz, 1H), 7.64 (d,J = 8.0 Hz, 1H), 7.57 (ddd,J = 8.4, 8.0, 1.2 Hz, 1H), 7.35 (ddd,J = 8.4, 8.0, 1.2 Hz, 1H), 6.93 (t,J = 4.8 Hz, 1H), 4.84 (t,J = 5.6 Hz, 1H), 3.66 (m, 4H).Examples 8 10- chlorine -6- (2- Hydroxyethoxy ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7718) : Synthesized according to the general procedure -G. Yield: 150 mg (56%). ES-MS [M + 1]⁺ : 357.9; t_R : 4.73 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.50 (d,J = 8.4 Hz, 1H), 8.33 (d,J = 2.4 Hz, 1H), 8.04 (d,J = 8.8 Hz, 1H), 7.86-7.81 (m, 2H), 7.70 (dd,J = 6.8, 4.8 Hz, 1H), 7.59 (t,J = 8.0 Hz, 1H), 4.93 (t,J = 5.6 Hz, 1H), 4.60 (t,J = 5.2 Hz, 2H), 3.85 (t,J = 5.2 Hz, 2H).Examples 9 10- chlorine -6- (3- Hydroxypropylamino ) -12H- Benzothioan and [2,3-c] quinoline -12- ketone (7719) : Synthesized according to the general procedure -D. Yield: 218 mg (78%). ES-MS [M + 1]⁺ : 370.9; t_R : 4.43 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.32 (d,J = 8.4 Hz, 1H), 8.35 (d,J = 2.4 Hz, 1H), 7.97 (d,J = 8.4 Hz, 1H), 7.86 (dd,J = 8.4, 2.4 Hz, 1H), 7.65 (d,J = 8.4 Hz, 1H), 7.57 (t,J = 8.0, 1H), 7.35 (dd,J = 8.0, 7.2 Hz, 1H), 7.13 (t,J = 4.8 Hz, 1H), 4.65 (dd,J = 5.2, 4.8 Hz, 1H), 3.62 (q,J = 6.0 Hz, 2H), 3.55 (q,J = 5.6 Hz, 2H), 1.84 (quint,J = 6.4 Hz, 2H).Examples 10 10- chlorine -6- (3- Methoxypropylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7720) : Synthesized according to the general procedure -D. Yield: 160 mg (55%). ES-MS [M + 1]⁺ : 384.9; t_R : 6.12 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.31 (d,J = 8.4 Hz, 1H), 8.33 (d,J = 2.4 Hz, 1H), 7.96 (d,J = 8.4 Hz, 1H), 7.84 (dd,J = 8.4, 2.4 Hz, 1H), 7.64 (d,J = 8.4 Hz, 1H), 7.56 (ddd,J = 8.4, 8.0, 1.2 Hz, 1H), 7.34 (ddd,J = 8.4, 8.0, 1.2 Hz, 1H), 7.12 (t,J = 4.8 Hz, 1H), 3.59 (q,J = 6.8 Hz, 2H), 3.46 (dd,J = 6.4, 6.0 Hz, 2H), 3.26 (s, 3H), 1.92 (quint,J = 6.4 Hz, 2H).Examples 11 10- chlorine -6- (3- ( Methylamine ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7721) : Synthesized according to the general procedure -D. Yield: 162 mg (56%). ES-MS [M + 1]⁺ : 384.0; t_R : 4.12 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.32 (d,J = 8.8 Hz, 1H), 8.36 (d,J = 2.0 Hz, 1H), 7.97 (d,J = 8.8 Hz, 1H), 7.87 (dd,J = 8.4, 2.4 Hz, 1H), 7.67 (d,J = 8.4 Hz, 1H), 7.58 (dd,J = 8.0, 7.2 Hz, 1H), 7.36 (dd,J = 8.0, 7.2 Hz, 1H), 3.63 (t,J = 6.4 Hz, 2H), 2.80 (dd,J = 7.2, 6.4 Hz, 2H), 2.43 (s, 3H), 1.91 (quint,J = 6.4 Hz, 2H).Examples 12 10- chlorine -6- (3- ( Dimethylamino ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7722) : Synthesized according to the general procedure -D. Yield: 275 mg (92%). ES-MS [M + 1]⁺ : 398.0; t_R : 5.76 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.34 (d,J = 8.0 Hz, 1H), 8.39 (s, 1H), 8.05 (d,J = 8.4 Hz, 1H), 7.90 (m, 2H), 7.66 (d,J = 8.0 Hz, 1H), 7.58 (dd,J = 8.0, 7.2 Hz, 1H), 7.36 (dd,J = 8.0, 7.6 Hz, 1H), 3.60 (q,J = 4.8 Hz, 2H), 2.41 (m, 2H), 2.24 (s, 6H), 1.82 (quint,J = 6.4 Hz, 2H).Examples 13 10- chlorine -6- ( Ethylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7736) : Synthesized according to the general procedure -D. Yield: 200 mg (49%). ES-MS [M + 1]⁺ : 340.9; t_R : 6.09 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.31 (d,J = 7.6 Hz, 1H), 8.33 (d,J = 2.0 Hz, 1H), 7.93 (d,J = 8.8 Hz, 1H), 7.83 (dd,J = 8.4, 2.4 Hz, 1H), 7.65 (d,J = 8.0 Hz, 1H), 7.56 (ddd,J = 8.0, 6.8, 1.2 Hz, 1H), 7.33 (ddd,J = 8.4, 6.8, 1.2 Hz, 1H), 7.10 (dd,J = 5.2, 4.8 Hz, 1H), 3.57 (m, 2H), 1.25 (t,J = 7.2 Hz, 3H).Examples 14 6- ( Benzylamino ) -10- chlorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7737) : Synthesized according to the general procedure -D. Yield: 205 mg (68%). ES-MS [M + 1]⁺ : 403.0; t_R : 6.51 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.33 (d,J = 8.4 Hz, 1H), 8.38 (d,J = 2.4 Hz, 1H), 8.00 (d,J = 8.8 Hz, 1H), 7.88 (dd,J = 8.8, 2.4 Hz, 1H), 7.82 (dd,J = 6.0, 5.2 Hz, 1H), 7.62 (d,J = 8.0 Hz, 1H), 7.56 (ddd,J = 8.0, 6.8, 1.2 Hz, 1H), 7.44 (d,J = 7.6 Hz, 2H), 7.36 (dt,J = 6.8, 1.2 Hz, 1H), 7.28 (dd,J = 8.0, 7.2 Hz, 2H), 4.79 (d,J = 5.6 Hz, 2H).Examples 15 6- (2- Aminoethylamino ) -10- chlorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7767) : Self-stent compound according to general procedure -E4a Begin synthesis. ES-MS [M + 1] +: 356.1; 1H NMR (400 MHz, DMSO-d6): δ 9.32 (1H, d,J = 8.4 Hz), 8.35 (1H, br), 7.96 (1H, d,J = 8.8 Hz), 7.85 (1H, t,J = 7.2 Hz), 7.66 (1H, d,J = 8.0 Hz), 7.59 (1H, t,J = 8.0 Hz), 7.36 (1H, t,J = 8.0 Hz), 3.59 (2H, t,J = 6.0 Hz), 2.90 (2H, t,J = 6.0 Hz).Examples 16 N- (10- chlorine -12- Pendant oxygen -12H- Benzothieno [2,3-c] quinoline -6- base ) Pyridoxamine (7801) : Use according to general procedure -K7702 synthesis. Yield: 120 mg (36%). ES-MS [M + 1]⁺ : 417.9; t_R : 4.77 minutes (Method-A),¹ H NMR (400 MHz, DMSO-d₆ ):δ 11.45 (s, 1H), 9.68 (dd,J = 8.4, 2.0 Hz, 1H), 8.82 (d,J = 4.8 Hz, 1H), 8.42 (d,J = 2.0 Hz, 1H), 8.17 (d,J = 7.6 Hz, 1H), 8.13-8.08 (m, 3H), 7.90-7.84 (m, 3H), 7.76 (dd,J = 6.4, 4.8 Hz, 1H). Scenario 2 Examples 17 6- chlorine -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (4b) : Starting from 4-fluorothiophenol, the general procedure A-C was followed in 3 steps. Yield: 54% over 3 steps. ES-MS [M + 1]⁺ : 315.9; tR: 5.84 minutes (Method-A).Examples 18 6- Amine -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7705) : Synthesized according to the general procedure -F. Yield: 165 mg (92%). ES-MS [M + 1]⁺ : 297.0; t_R : 3.53 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.41 (d,J = 8.4 Hz, 1H), 8.17 (dd,J = 9.6, 2.4 Hz, 1H), 8.04 (dd,J = 8.8, 5.2 Hz, 1H), 7.78 (ddd,J = 8.4, 8.0, 2.8 Hz, 1H), 7.66-7.58 (m, 2H), 7.39 (dd,J = 8.0, 7.2 Hz, 1H), 7.08 (brs, 2H).Examples 19 10- fluorine -6- ( Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7706) : Synthesized according to the general procedure -D. Yield: 190 mg (71%). ES-MS [M + 1]⁺ : 339.0; t_R : 5.87 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.38 (d,J = 8.4 Hz, 1H), 8.17 (dd,J = 9.6, 2.8 Hz, 1H), 8.06 (m, 1H), 7.79 (td,J = 8.4, 2.8 Hz, 1H), 7.69 (d,J = 7.4 Hz, 1H), 7.61 (t,J = 7.0 Hz, 1H), 7.37 (t,J = 7.0 Hz, 1H), 7.13 (t,J = 5.2 Hz, 1H), 3.55 (q,J = 6.4 Hz, 2H), 1.74 (q,J = 7.2 Hz, 2H), 0.97 (t,J = 7.2 Hz, 3H).Examples 20 6- (3- Aminopropylamino ) -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7707) : Synthesized according to the general procedure -E. Yield: 210 mg (75%). ES-MS [M + 1]⁺ : 354.0; t_R : 2.35 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.36 (d,J = 8.4 Hz, 1H), 8.15 (dd,J = 9.6, 2.8 Hz, 1H), 8.02 (dd,J = 8.8, 5.2 Hz, 1H), 7.76 (ddd,J = 8.8, 8.0, 2.8 Hz, 1H), 7.68 (d,J = 8.0 Hz, 1H), 7.58 (dd,J = 7.2, 6.8 Hz, 1H), 7.36 (t,J = 7.2 Hz, 1H), 3.65 (t,J = 6.8 Hz, 2H), 2.78 (t,J = 6.8 Hz, 2H), 1.86 (quint,J = 6.8 Hz, 2H).Examples 21 10- fluorine -6- (3- (2- Hydroxyethylamino ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7708) : Synthesized according to the general procedure -D. Yield: 260 mg (69%). ES-MS [M + 1]⁺ : 398.0; t_R : 2.42 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.36 (d,J = 8.4 Hz, 1H), 8.14 (dd,J = 9.6, 2.8 Hz, 1H), 8.00 (dd,J = 8.8, 4.8 Hz, 1H), 7.76 (ddd,J = 8.8, 8.4, 2.8 Hz, 1H), 7.67 (d,J = 8.0 Hz, 1H), 7.58 (d,J = 7.2, 1H), 7.35 (dd,J = 7.6, 7.2 Hz, 1H), 4.81 (brs, 1H), 3.63 (t,J = 6.4 Hz, 2H), 3.57 (t,J = 5.6 Hz, 2H), 2.82 (t,J = 6.4 Hz, 2H), 2.75 (dd,J = 6.0, 5.2 Hz, 2H), 1.90 (quint,J = 6.4 Hz, 2H).Examples twenty two 10- fluorine -6- (2- Hydroxyethylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7727) : Synthesized according to the general procedure -D. Yield: 180 mg (55%). ES-MS [M + 1]⁺ : 340.9; t_R : 3.55 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.32 (d,J = 7.6 Hz, 1H), 8.09 (dd,J = 9.6, 2.8 Hz, 1H), 8.00 (dd,J = 8.8, 5.2 Hz, 1H), 7.73 (ddd,J = 8.8, 8.4, 2.8 Hz, 1H), 7.65 (d,J = 7.6 Hz, 1H), 7.57 (ddd,J = 8.4, 7.6, 1.6 Hz, 1H), 7.34 (dt,J = 8.4, 1.6 Hz, 1H), 6.97 (brs, 1H), 3.70-3.64 (m, 4H).Examples 23 10- fluorine -6- (2- Hydroxyethoxy ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7728) : Synthesized according to the general procedure -D. Yield: 180 mg (33%). ES-MS [M + 1]⁺ : 342.0; t_R : 4.09 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.56 (dd,J = 8.4, 1.2 Hz, 1H), 8.16-8.11 (m, 2H), 7.84 (ddd,J = 8.4, 8.0, 1.2 Hz, 1H), 7.79-7.69 (m, 2H), 7.59 (ddd,J = 7.2, 6.8, 1.2 Hz, 1H), 4.95 (dd,J = 5.6, 5.2 Hz, 1H), 4.62 (dd,J = 5.2, 4.8 Hz, 2H), 3.85 (q,J = 5.2 Hz, 2H).Examples 24 10- fluorine -6- (3- Hydroxypropylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7729) : Synthesized according to the general procedure -D. Yield: 247 mg (73%). ES-MS [M + 1]⁺ : 355.0; t_R : 3.79 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.34 (d,J = 8.0 Hz, 1H), 8.10 (dd,J = 9.6, 2.8 Hz, 1H), 8.00 (dd,J = 8.8, 5.2 Hz, 1H), 7.73 (dt,J = 8.8, 2.8 Hz, 1H), 7.65 (d,J = 7.2 Hz, 1H), 7.56 (dt,J = 8.0, 1.2 Hz, 1H), 7.33 (dt,J = 8.4, 1.2 Hz, 1H), 7.10 (d,J = 4.8 Hz, 1H), 4.65 (brs, 1H), 3.62 (m, 2H), 3.55 (t,J = 6.0 Hz, 2H), 1.84 (quint,J = 6.4 Hz, 2H).Examples 25 10- fluorine -6- (3- Methoxypropylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7730) : Synthesized according to the general procedure -D. Yield: 150 mg (51%). ES-MS [M + 1]⁺ : 369.0; t_R : 5.49 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.4 Hz, 1H), 8.13 (d,J = 9.2 Hz, 1H), 8.03 (m, 1H), 7.75 (t,J = 7.2 Hz, 1H), 7.66 (d,J = 8.0 Hz, 1H), 7.57 (dd,J = 7.6, 6.8 Hz, 1H), 7.35 (dd,J = 8.0, 7.2 Hz, 1H), 7.12 (brs, 1H), 3.60 (q,J = 5.2 Hz, 2H), 3.46 (t,J = 5.6 Hz, 2H), 3.26 (s, 3H), 1.93 (quint,J = 6.4 Hz, 2H).Examples 26 10- fluorine -6- (3- ( Methylamine ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7731) : Synthesized according to the general procedure -D. Yield: 137 mg (47%). ES-MS [M + 1]⁺ : 368.0; t_R : 3.29 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.4 Hz, 1H), 8.14 (dd,J = 9.6, 2.4 Hz, 1H), 8.03 (dd,J = 8.8, 4.8 Hz, 1H), 7.76 (ddd,J = 8.8, 8.4, 2.8 Hz, 1H), 7.66 (d,J = 8.0 Hz, 1H), 7.57 (dd,J = 8.0, 6.8 Hz, 1H), 7.34 (dd,J = 8.0, 7.6 Hz, 1H), 7.30 (brs, 1H), 3.62 (t,J = 6.4 Hz, 2H), 2.64 (t,J = 6.4 Hz, 2H), 2.33 (s, 3H), 1.81 (quint,J = 6.4 Hz, 2H).Examples 27 6- (3- ( Dimethylamino ) Propylamino ) -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7732) : Synthesized according to the general procedure -D. Yield: 240 mg (66%). ES-MS [M + 1]⁺ : 382.0; t_R : 3.86 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.36 (d,J = 8.4 Hz, 1H), 8.15 (dd,J = 9.6, 2.8 Hz, 1H), 8.05 (dd,J = 8.8, 4.8 Hz, 1H), 7.77 (ddd,J = 8.8, 8.4, 2.8 Hz, 1H), 7.67 (d,J = 8.4 Hz, 1H), 7.62-7.56 (m, 2H), 7.36 (ddd,J = 8.4, 8.0, 1.2 Hz, 1H), 3.62 (m, 2H), 2.77 (m, 2H), 2.49 (s, 6H), 1.94 (quint,J = 6.8 Hz, 2H).Examples 28 10- fluorine -6- (3- Morpholinylpropylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7741) : Synthesized according to the general procedure -D. Yield: 297 mg (72%). ES-MS [M + 1]⁺ : 424.0; t_R : 5.13 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.37 (d,J = 8.4 Hz, 1H), 8.16 (dd,J = 9.6, 2.8 Hz, 1H), 8.02 (dd,J = 8.8, 4.8 Hz, 1H), 7.78 (td,J = 8.0, 2.8 Hz, 1 H), 7.65 (d,J = 8.0 Hz, 1H), 7.58 (ddd,J = 8.4, 7.6, 1.2 Hz, 1H), 7.38-7.33 (m, 2H), 3.62 (m, 6H), 2.46-2.41 (m, 6H), 1.85 (d,J = 6.8 Hz, 2H).Examples 29 10- fluorine -6- (2- Methoxyethylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7745) : Synthesized according to the general procedure -D. Yield: 170 mg (50%). ES-MS [M + 1]⁺ : 355.0; t_R : 2.8 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.34 (d,J = 8.8 Hz, 1H), 8.12 (dd,J = 9.6, 2.4 Hz, 1H), 8.03 (dd,J = 9.2, 5.2 Hz, 1H), 7.75 (td,J = 8.4, 2.8 Hz, 1 H), 7.66 (d,J = 8.0 Hz, 1H), 7.57 (t,J = 7.6 Hz, 1H), 7.35 (t,J = 7.6 Hz, 1H), 7.02 (brs, 1H), 3.74 (q,J = 5.6 Hz, 2H), 3.62 (t,J = 5.6 Hz, 2H).Examples 30 10- fluorine -6- ( Hexahydropyridine -1- base ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7746) : Synthesized according to the general procedure -D. Yield: 118 mg (34%). ES-MS [M + 1]⁺ : 365.0; t_R : 4.57 minutes (Method-D);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.56 (d,J = 8.4 Hz, 1H), 8.16 (dd,J = 9.6, 2.8 Hz, 1H), 8.13 (dd,J = 9.2, 5.2 Hz, 1H), 7.93 (d,J = 8.4 Hz, 1 H), 7.78-7.73 (m, 2H), 7.64 (t,J = 7.2 Hz, 1H), 3.24 (t,J = 4.4 Hz, 4H), 1.79-1.76 (m, 4H), 1.65 (m, 2H).Examples 31 10- fluorine -6- ( Pyrrolidine -1- base ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7747) : Synthesized according to the general procedure -D. Yield: 166 mg (49%). ES-MS [M + 1]⁺ : 350.9; t_R : 6.76 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.4 Hz, 1H), 8.11 (dd,J = 9.6, 2.8 Hz, 1H), 8.06 (dd,J = 8.8, 5.2 Hz, 1H), 7.77-7.23 (m, 2H), 7.65 (dd,J = 8.0, 7.2 Hz, 1H), 7.46 (dd,J = 8.0, 7.2 Hz, 1H), 3.70 (m, 4H), 1.94 (m, 4H).Examples 32 10- fluorine -6- Morpholinyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (7738) : Synthesized according to the general procedure -D. Yield: 160 mg (55%). ES-MS [M + 1]⁺ : 367.0; t_R : 5.43 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.56 (d,J = 8.4 Hz, 1H), 8.17-8.10 (m, 2H), 7.95 (d,J = 8.0 Hz, 1H), 7.79-7.74 (m, 2H), 7.66 (t,J = 7.2 Hz, 1H), 3.88 (m, 4H), 3.3 (m, 4H; found to be combined with H-O-D signals).Examples 33 10- fluorine -6- ( Hexahydropyrazine -1- base ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7739) : According to the modified general procedure -F uses 1 in the first stage- Boc-hexahydropyrazine was synthesized instead of 4-methoxybenzyl. Yield: 310 mg (56% over 2 steps). ES-MS [M + 1]⁺ : 366.0; t_R : 3.6 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.53 (d,J = 8.4 Hz, 1H), 8.14-8.07 (m, 2H), 7.92 (d,J = 8.0 Hz, 1H), 7.77-7.71 (m, 2H), 7.63 (ddd,J = 8.4, 8.0, 1.0 Hz, 1H), 3.20 (m, 4H), 2.97 (m, 4H).Examples 34 10- fluorine -6- (4- Methylhexahydropyrazine -1- base ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7740) : Synthesized according to the general procedure -D. Yield: 175 mg (48%). ES-MS [M + 1]⁺ : 380.0; t_R : 3.69 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.51 (d,J = 8.4 Hz, 1H), 8.1 (dd,J = 9.6, 2.4 Hz, 1H), 8.07 (dd,J = 8.8, 4.8 Hz, 1H), 7.91 (d,J = 8.4 Hz, 1H), 7.76-7.70 (m, 2H), 7.61 (ddd,J = 8.4, 7.2, 1.2 Hz, 1H), 3.29 (m, 4H, combined with H-O-D signals), 2.63 (m, 4H), 2.31 (s, 3H).Examples 35 10- fluorine -6- ( Pyridine -3- Methylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7748) : Synthesized according to the general procedure -D. Yield: 200 mg (54%). ES-MS [M + 1]⁺ : 387.9; t_R : 4.33 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.4 Hz, 1H), 8.69 (s, 1H), 8.38 (d,J = 4.0 Hz, 1H), 8.13 (dd,J = 9.6, 2.8 Hz, 1H), 8.03 (dd,J = 8.8, 5.2 Hz, 1H), 7.90-7.78 (m, 2H), 7.77-7.73 (m, 1H), 7.65 (d,J = 7.6 Hz, 1H), 7.56 (t,J = 7.2 Hz, 1H), 7.35 (t,J = 7.6 Hz, 1H), 7.3 (dd,J = 7.6, 4.8 Hz, 1H), 4.77 (d,J = 5.6 Hz, 2H).Examples 36 6- ( Benzylamino ) -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7749) : Synthesized according to the general procedure -D. Yield: 127 mg (41.5%). ES-MS [M + 1]⁺ : 386.9; t_R : 5.72 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.8 Hz, 1H), 8.14 (dd,J = 9.2, 2.8 Hz, 1H), 8.04 (dd,J = 8.8, 4.8 Hz, 1H), 7.8-7.74 (m, 2H), 7.63 (d,J = 8.0 Hz, 1H), 7.55 (t,J = 8.0 Hz, 1H), 7.44 (d,J = 8.0 Hz, 2H), 7.35 (t,J = 8.8 Hz, 1H), 7.28 (t,J = 8.0 Hz, 2H), 7.18 (t,J = 7.6 Hz, 1H), 4.78 (d,J = 5.6 Hz, 2H).Examples 37 6- (2- ( Dimethylamino ) Ethylamino ) -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7744) : Synthesized according to the general procedure -D. Yield: 210 mg (60%). ES-MS [M + 1]⁺ : 367.9; t_R : 3.94 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.4 Hz, 1H), 8.14 (dd,J = 10.0, 2.8 Hz, 1H), 8.07 (dd,J = 8.8, 5.2 Hz, 1H), 7.76 (td,J = 8.4, 2.8 Hz, 1 H), 7.67 (d,J = 7.6 Hz, 1H), 7.58 (t,J = 7.2 Hz, 1H), 7.36 (t,J = 7.2 Hz, 1H), 6.85 (brs, 1H), 3.65 (q,J = 6.0 Hz, 2H), 2.57 (t,J = 6.4 Hz, 2H), 2.23 (s, 6H).Examples 38 10- fluorine -6- (1H- Pyrrole -1- base ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7750) : According to the general procedure -H self-stent compound4b Begin synthesis. Yield: 96 mg (27%). ES-MS [M + 1]⁺ : 346.9; t_R : 7.21 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.59 (d,J = 8.4 Hz, 1H), 8.16 (dd,J = 9.6, 2.8 Hz, 1H), 8.09 (m, 2H), 7.85 (m, 2H), 7.76 (td,J = 8.4, 2.8 Hz, 1H), 7.40 (m, 2H), 6.41 (m, 2H).Examples 39 10- fluorine -6- (2- ( Methylamine ) Ethylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7752) : -D self scaffold compound according to general procedure4b Begin synthesis. Yield: 165 mg (49%). ES-MS [M + 1] +: 353.9; tR: 4.12 minutes (Method-E), 1H NMR (400 MHz, DMSO-d₆ ): δ 9.38 (d, J = 8.0 Hz, 1H), 8.94 (brs, 1H), 8.16 (dd, J = 10.0, 2.8 Hz, 1H), 8.05 (dd, J = 9.2, 8.8 Hz, 1H), 7.79-7.74 (m, 2H), 7.62 (dd, J = 7.2, 6.8 Hz, 1H), 7.48 (t, J = 5.2 Hz, 1H), 7.41 (dd, J = 7.6, 7.2 Hz, 1H), 3.88 (m, 2H), 3.25 (m, 2H), 2.59 (s, 3H).Examples 40 10- fluorine -6- (3- ( Pyrrolidine -1- base ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7753) : -D self scaffold compound according to general procedure4b Begin synthesis. Yield: 125 mg (32%). ES-MS [M + 1]⁺ : 408.0; t_R : 3.39 minutes (Method-E), 1H NMR (400 MHz, DMSO-d₆ ):δ 9.37 (d,J = 8.4 Hz, 1H), 8.15 (dd,J = 9.6, 2.8 Hz, 1H), 8.01 (dd,J = 8.4, 4.4 Hz, 1H), 7.78 (td,J = 8.4, 2.8 Hz, 1H), 7.69 (d,J = 8.0 Hz, 1H), 7.60 (t,J = 6.8 Hz, 1H), 7.47 (brs, 1H), 7.38 (t,J = 7.6 Hz, 1H), 3.65 (q,J = 4.8 Hz, 2H), 3.1 (brs, 4H), 2.05 (t,J = 6.0 Hz, 2H), 1.88 (brs, 4H).Examples 41 6- (2- Aminoethylamino ) -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7754) : Self-stent compound according to general procedure -E4b Begin synthesis. Yield: 115 mg (36%). ES-MS [M + 1] +: 340.0; tR: 4.69 minutes (Method-E), 1H NMR (400 MHz, DMSO-d₆ ): δ 9.38 (d, J = 8.4 Hz, 1H), 8.15 (d, J = 9.6 Hz, 1H), 8.06 (m, 1H), 7.78 (m, 1H), 7.72 (d, J = 8.0 Hz, 1H), 7.61 (dd, J = 7.6, 7.2 Hz, 1H), 7.40 (t, J = 7.6 Hz, 1H), 3.75 (m, 2H), 3.08 (m, 2H).Examples 42 10- fluorine -6- (2- ( Pyrrolidine -1- base ) Ethylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7755) : -D self scaffold compound according to general procedure4b Begin synthesis. Yield: 82 mg (22%). ES-MS [M + 1]⁺ : 394.1; t_R : 3.34 minutes (Method-E), 1H NMR (400 MHz, DMSO-d₆ ):δ 9.39 (d,J = 8.4 Hz, 1H), 8.17 (dd,J = 9.6, 4.8 Hz, 1H), 8.06 (dd,J = 8.8, 4.8 Hz, 1H), 7.79 (ddd,J = 8.8, 8.4, 2.8 Hz, 1H), 7.73 (d,J = 7.6 Hz, 1H), 7.63 (t,J = 6.8 Hz, 1H), 7.55 (brs, 1H), 7.42 (dd,J = 8.4, 7.2 Hz, 1H), 3.93 (m, 2H), 3.67 (brs, 2H), 3.47 (m, 2H), 3.09 (m, 2H), 1.99 (brs, 2H), 1.87 (brs, 2H) .Examples 43 10- fluorine -6-((2- Morpholinylethyl ) Amine ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7756) : -D self scaffold compound according to general procedure4b Begin synthesis. Yield: 194 mg (50%). ES-MS [M + 1]⁺ : 409.9; t_R : 4.08 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.36 (d,J = 8.0 Hz, 1H), 8.14 (dd,J = 10.0, 2.8 Hz, 1H), 8.06 (dd,J = 9.2, 5.2 Hz, 1H), 7.77 (ddd,J = 8.8, 8.4, 2.8 Hz, 1H), 7.67 (d,J = 7.6 Hz, 1H), 7.58 (dd,J = 7.2, 6.8 Hz, 1H), 7.36 (t,J = 7.2 Hz, 1H), 6.98 (m, 1H), 3.68 (m, 2H), 3.58 (m, 4H), 2.47 (m, 4H; combined with residual DMSO signal), 2.63 (t,J = 6.4 Hz, 2H).Examples 44 4- (10- fluorine -12- Pendant oxygen -12H- Benzothieno [2,3-c] quinoline -6- base ) Hexahydro Pyrazine -1- Tert-butyl formate (7764) : -D self scaffold compound according to general procedure4b Begin synthesis. Yield: 230 mg (53%). ES-MS [M + 1]⁺ : 465.9; t_R : 7.57 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.55 (d,J = 8.4 Hz, 1H), 8.14 (d,J = 10.0 Hz, 1H), 8.09 (m, 1H), 7.93 (d,J = 8.4 Hz, 1H), 7.76 (m, 2H), 7.65 (dd,J = 8.4, 7.2 Hz, 1H), 3.61 (brs, 4H), 3.25 (m, 4H), 1.43 (s, 9H).Examples 45 6- (4- Ethyl hexahydropyrazine -1- base ) -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7757) : Synthesized according to the general procedure-I in the presence of iodoethane. Yield: 160 mg (49%). ES-MS [M + 1]⁺ : 394.0; t_R : 4.37 minutes (Method-F),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.53 (d,J = 8.4 Hz, 1H), 8.14-8.07 (m, 2H), 7.92 (d,J = 8.0 Hz, 1H), 7.77-7.72 (m, 2H), 7.64 (dd,J = 8.0, 7.6 Hz, 1H), 2.70-2.64 (m, 2H), 1.08 (m, 3H).Examples 46 6- (4- Benzylhexahydropyrazine -1- base ) -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7758) : Synthesized according to the general procedure-I in the presence of chlorotoluene. Yield: 152 mg (61%). ES-MS [M + 1]⁺ : 456.0; t_R : 4.59 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.54 (d,J = 8.8 Hz, 1H), 8.15-8.07 (m, 2H), 7.93 (d,J = 8.0 Hz, 1H), 7.74 (dd,J = 8.0, 7.6 Hz, 2H), 7.64 (dd,J = 8.0, 7.6 Hz, 1H), 7.38-7.32 (m, 4H), 7.26 (m, 1H), 3.62 (s, 2H), 3.32 (m, 4H), 2.69 (m, 4H).Examples 47 10- fluorine -6- (1H- Pyrazole -1- base ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7759) : Synthesized according to a modified general procedure -H, where K is used separately₂ CO₃ , L-proline and CuI as base, ligand and catalyst. Yield: 168 mg (51%). ES-MS [M + 1]⁺ : 347.9; t_R : 6.96 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.44 (d,J = 8.8 Hz, 1H), 8.64 (d,J = 2.4 Hz, 1H), 8.13-8.05 (m, 3H), 8.02 (d,J = 1.6 Hz, 1H), 7.89 (dd,J = 10.0, 8.4 Hz, 1H), 7.83 (dd,J = 8.0, 6.8 Hz, 1H), 7.75 (td,J = 8.8, 2.8 Hz, 1H), 6.74 (t,J = 2.4 Hz, 1H).Examples 48 10- fluorine -6- ( Pyridine -2- Amino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7760) : -H self scaffold compound following general procedure4b Begin synthesis. Yield: 200 mg (25%). ES-MS [M + 1]⁺ : 373.9; t_R : 5.98 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.43 (d,J = 7.2 Hz, 1H), 8.35 (brs, 1H), 8.18-8.12 (m, 2H), 7.87-7.76 (m, 4H), 7.62 (m, 1H), 7.39 (m, 1H), 7.23 (d,J = 7.2 Hz, 1H), 7.00 (m, 1H).Examples 49 10- fluorine -6- ( Pyridine -3- Amino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7761) : According to the general procedure -H self-stent compound4b Begin synthesis. Yield: 82 mg (23%). ES-MS [M + 1]⁺ : 373.9; t_R : 4.19 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.47 (d,J = 8.4 Hz, 1H), 9.23 (brs, 1H), 8.91 (d,J = 2.0 Hz, 1H), 8.25 (d,J = 4.4 Hz, 1H), 8.19 (dd,J = 9.6, 2.8 Hz, 1H), 8.14-8.11 (m, 2H), 7.81 (td,J = 8.4, 2.8 Hz, 1H), 7.73 (d,J = 7.6 Hz, 1H), 7.67 (t,J = 7.2 Hz, 1H), 7.53 (dd,J = 8.0, 7.2 Hz, 1H), 7.38 (dd,J = 8.4, 4.4 Hz, 1H)Examples 50 10- fluorine -6- ( Phenylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7762) : -D self scaffold compound according to general procedure4b Begin synthesis. Yield: 85 mg (23%). ES-MS [M + 1]⁺ : 372.9; t_R : 3.59 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.45 (d,J = 8.4 Hz, 1H), 8.99 (s, 1H), 8.17 (dd,J = 9.6, 2.8 Hz, 1H), 8.12-8.09 (m, 1H), 7.78 (td,J = 8.8, 2.8 Hz, 1H), 7.72-7.63 (m, 4H), 7.50 (td,J = 8.4, 1.2 Hz, 1H), 7.34 (m, 2H), 7.04 (t,J = 7.2 Hz, 1H).Examples 51 10- fluorine -6- ( Pyridine -4- Amino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7763) : According to the general procedure -H self-stent compound4b Begin synthesis. Yield: 189 mg (53%). ES-MS [M + 1]⁺ : 373.9; t_R : 5.57 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.54 (brs, 1H), 9.52 (d,J = 8.4 Hz, 1H), 8.34 (m, 2H), 8.18 (dd,J = 9.6, 2.8 Hz, 1H), 8.14 (m, 1H), 7.85-7.80 (m, 2H), 7.72 (m, 1H), 7.63 (m, 3H).Examples 51 10- fluorine -6-((2- ( Pyridine -2- Amino ) Ethyl ) Amine ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7765) : Self-stent compound according to general procedure -D4b Begin synthesis. Yield: 115 mg (27%). ES-MS [M + 1]⁺ : 417.0; t_R : 6.67 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ): δ 9.36 (d,J = 8.0 Hz, 1H), 8.14 (dd,J = 10.0, 2.8 Hz, 1H), 8.11-8.05 (m, 2H), 7.77 (td,J = 8.4, 2.8 Hz, 1H), 7.70-7.67 (m, 2H), 7.58 (td,J = 7.6, 1.2 Hz, 1H), 7.4-7.34 (m, 2H), 6.85 (m, 1H), 6.56-6.49 (m, 2H), 3.72 (q,J = 5.2 Hz, 2H), 3.59 (q,J = 5.2 Hz, 2H).Examples 52 10- fluorine -6- (1H- Imidazole -1- base ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7766) : According to the general procedure -H self-stent compound4b Begin synthesis. Yield: 105 mg (31%). ES-MS [M + 1]⁺ : 348.0; t_R : 5.29 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.71 (s, 1H), 8.31-8.19 (m, 4H), 7.96 (m, 2H), 7.84 (m, 2H), 7.28 (s, 1H). Option 3 Examples 53 6- chlorine -10- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (4c) : Starting from 4-methoxythiophenol, the general procedure A-C was followed in 3 steps. Yield: 51% over 3 steps. ES-MS [M + 1]⁺ : 327.9; t_R : 5.95 minutes (Method-A).Examples 54 6- Amine -10- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7709) : Synthesized according to the general procedure -F. Yield: 195 mg (84%). ES-MS [M + 1]⁺ : 309.0; t_R : 3.29 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.46 (d,J = 8.5 Hz, 1H), 7.95 (d,J = 2.7 Hz, 1H), 7.89 (d,J = 8.8 Hz, 1H), 7.66 (d,J = 8.0 Hz, 1H), 7.6 (t,J = 7.7 Hz, 1H), 7.5 (dd,J = 8.8, 2.8 Hz, 1H), 7.39 (t,J = 8.2 Hz, 1H), 7.02 (brs, 2H), 3.94 (s, 3H).Examples 55 10- Methoxy -6- ( Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7710) : Synthesized according to the general procedure -D. Yield: 120 mg (45%). ES-MS [M + 1]⁺ : 351.0; t_R : 5.71 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.40 (d,J = 8.4, 1H), 7.91 (d,J = 2.8 Hz, 1H), 7.86 (d,J = 8.8, 1H), 7.66 (dd,J = 8.4, 1.2 Hz, 1H), 7.56 (ddd,J = 8.4, 6.8, 1.2 Hz, 1H), 7.46 (td,J = 8.4, 2.8 Hz, 1H), 7.34 (ddd,J = 8.4, 6.8, 1.2 Hz, 1H), 7.08 (dd,J = 4.8, 5.2 Hz, 1H), 3.91 (s, 3H), 3.52 (m, 2H), 1.70 (sextet,J = 7.2 Hz, 2H), 0.94 (t,J = 7.2 Hz, 3H). Example 566- (3- Aminopropylamino ) -10- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7711) : Synthesized according to the general procedure -E. Yield: 130 mg (46%). ES-MS [M + 1]⁺ : 366.0; t_R : 2.12 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.43 (d,J = 8.0 Hz, 1H), 7.94 (d,J = 2.8 Hz, 1H), 7.88 (d,J = 8.8 Hz, 1H), 7.70 (d,J = 8.0 Hz, 1H), 7.6 (td,J = 7.0, 1.2 Hz, 1H), 7.50 (dd,J = 8.8, 2.8 Hz, 1H), 7.37 (t,J = 7.2 Hz, 1H), 3.94 (s, 3H), 3.67 (t,J = 6.4 Hz, 2H), 2.79 (t,J = 6.8 Hz, 2H), 1.86 (t,J = 6.4 Hz, 2H).Examples 57 6- (3- (2- Hydroxyethylamino ) Propylamino ) -10- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7712) : Synthesized according to the general procedure -D. Yield: 320 mg (72%). ES-MS [M + 1]⁺ : 410.0; t_R : 2.04 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.43 (d,J = 8.0 Hz, 1H), 7.93 (d,J = 2.0 Hz, 1H), 7.86 (d,J = 8.8 Hz, 1H), 7.70 (d,J = 8.0 Hz, 1H), 7.58 (t,J = 7.2 Hz, 1H), 7.5 (dd,J = 8.8, 2.8 Hz, 1H), 7.36 (t,J = 8.0 Hz, 1H), 3.93 (m, 4H), 3.66 (t,J = 6.4 Hz, 2H), 3.59 (t,J = 5.4 Hz, 2H), 2.84 (t,J = 6.4 Hz, 2H), 2.77 (t,J = 5.4 Hz, 2H), 1.92 (t,J = 6.4 Hz, 2H).Examples 58 6- (2- Hydroxyethylamino ) -10- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7733) : Synthesized according to the general procedure -D. Yield: 200 mg (62%). ES-MS [M + 1]⁺ : 353.0; t_R : 3.25 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.40 (d,J = 8.4 Hz, 1H), 7.90 (d,J = 3.2 Hz, 1H), 7.87 (d,J = 8.8 Hz, 1H), 7.66 (d,J = 8.0 Hz, 1H), 7.57 (dd,J = 7.6, 7.2 Hz, 1H), 7.46 (dd,J = 8.4, 2.8 Hz, 1H), 7.35 (dd,J = 8.0, 7.6 Hz, 1H), 6.92 (t,J = 4.4 Hz, 1H), 4.84 (brs, 1H), 3.91 (s, 3H), 3.65 (m, 4H).Examples 59 10- Methoxy -6- (3- Hydroxypropylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7742) : Synthesized according to the general procedure -D. Yield: 210 mg (75%). ES-MS [M + 1]⁺ : 366.9; t_R : 3.50 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.39 (d,J = 8.0 Hz, 1H), 7.89 (d,J = 3.2 Hz, 1H), 7.84 (d,J = 8.8 Hz, 1H), 7.65 (d,J = 8.0 Hz, 1H), 7.56 (ddd,J = 8.4, 6.8, 1.2 Hz, 1H), 7.44 (dd,J = 8.8, 2.8 Hz, 1H), 7.34 (dt,J = 8.4, 1.2 Hz, 1H), 7.08 (d,J = 4.8 Hz, 1H), 4.70 (brs, 1H), 3.90 (s, 3H), 3.62 (m, 2H), 3.55 (t,J = 6.4 Hz, 2H), 1.84 (quint,J = 6.4 Hz, 2H).Examples 60 10- Methoxy -6- (3- Methoxypropylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7743) : Synthesized according to the general procedure -D. Yield: 170 mg (59%). ES-MS [M + 1]⁺ : 381.0; t_R : 5.08 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.40 (d,J = 8.4 Hz, 1H), 7.91 (d,J = 2.8 Hz, 1H), 7.87 (d,J = 8.8 Hz, 1H), 7.66 (d,J = 8.4 Hz, 1H), 7.56 (t,J = 6.8 Hz, 1H), 7.46 (dd,J = 8.8, 2.8 Hz, 1H), 7.35 (dd,J = 7.2, 6.8 Hz, 1H), 7.09 (t,J = 5.2 Hz, 1H), 3.91 (s, 3H), 3.61 (m, 2H), 3.46 (t,J = 6.0 Hz, 2H), 3.26 (s, 3H), 1.93 (quint,J = 6.8 Hz, 2H).Examples 61 10- Methoxy -6- (3- ( Methylamine ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7734) : Synthesized according to the general procedure -D. Yield: 160 mg (69%). ES-MS [M + 1]⁺ : 380.0; t_R : 3.02 minutes (Method-C);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.41 (d,J = 8.4 Hz, 1H), 8.68 (brs, 1H), 7.92 (s, 1H), 7.87 (d,J = 8.8 Hz 1H), 7.70 (d,J = 7.6 Hz, 1H), 7.59 (dd,J = 8.0, 6.8 Hz, 1H), 7.49 (d,J = 8.8 Hz, 1H), 7.39-7.35 (m, 2H), 3.92 (s, 3H), 3.65 (q,J = 5.6 Hz, 2H), 2.96 (m, 2H), 2.52 (brs, 3H), 2.03 (m, 2H).Examples 62 6- (3- ( Dimethylamino ) Propylamino ) -10- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7735) : Synthesized according to the general procedure -D. Yield: 100 mg (33%). ES-MS [M + 1]⁺ : 394.0; t_R : 4.24 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.40 (d,J = 8.4 Hz, 1H), 7.9 (s, 1H), 7.88 (d,J = 8.8 Hz, 1H), 7.75 (brs, 1H), 7.65 (d,J = 8.4 Hz, 1H), 7.55 (t,J = 7.6 Hz, 1H), 7.45 (dd,J = 8.8, 2.8 Hz, 1H), 7.33 (dd,J = 8.0, 7.2 Hz, 1H), 3.91 (s, 3H), 3.60 (m, 2H), 2.40 (t,J = 6.0 Hz, 2H), 2.23 (s, 6H), 1.82 (quint,J = 6.0 Hz, 2H). Option 4 Examples 63 6,9- Dichloro -12H- Benzothieno [2,3-c] quinoline -12- Ketones and 6,11- Dichloro -12H- Benzothieno [2,3-c] quinoline -12- Ketone mixture (4d / 4d2) : Starting from 3-chlorothiophenol, the general procedure A-C was followed in 3 steps. Isomeric mixture formed4d /4d2 It cannot be further purified and is therefore used in analog formation. Yield: 49% over 3 steps. ES-MS [M + 1]⁺ : 331.9 and 331.9; t_R : 5.52 and 7.08 minutes (Method-A).Examples 64 6- Amine -9- chlorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7723) : According to the general procedure4d / 4d2 The mixture started to synthesize. However, the6q1 and6q2 The crude mixture was purified to individual isomers and further implementation started with isomer-1 (non-polar compared to isomer-2)6q1 Of preparation. Yield: 170 mg (stage-2: 78%). ES-MS [M + 1]⁺ : 312.9; t_R : 3.99 minutes (Method-A);¹ H NMR (400 MHz, TFA-d₁ ):δ 9.74 (d,J = 8.8 Hz, 1H), 8.95 (d,J = 8.8 Hz, 1H), 8.26 (m, 2H), 8.15 (m, 3H).Examples 65 6- Amine -11- chlorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7724) : According to the general procedure4d / 4d2 The mixture started to synthesize. However, the6q1 and6q2 The crude mixture was purified to individual isomers and further implementation was started with isomer-2 (compared to isomer-1).6q2 Of preparation. Yield: 60 mg (stage-2: 40%). ES-MS [M + 1]⁺ : 312.9; t_R : 3.24 minutes (Method-A);¹ H NMR (400 MHz, TFA-d₁ ):δ 9.20 (d,J = 8.4 Hz, 1H), 8.31 (m, 1H), 8.20-8.12 (m, 5H).Examples 66 9- chlorine -6- ( Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7725) : According to the general procedure4d / 4d2 The mixture started to synthesize. Nonpolar products of the two isomers present in the crude mixture were separated by the FCC and confirmed as6r1 . Yield: 195 mg. ES-MS [M + 1]⁺ : 355.0; t_R : 6.60 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.31 (d,J = 8.0 Hz, 1H), 8.40 (d,J = 8.8 Hz, 1H), 8.09 (d,J = 1.6 Hz, 1H), 7.69 (dd,J = 8.8, 2.0 Hz, 1H), 7.66 (d,J = 8.4 Hz, 1H), 7.57 (ddd,J = 8.4, 8.0, 1.6 Hz, 1H), 7.34 (td,J = 8.4, 1.6 Hz, 1H), 7.09 (t,J = 5.6 Hz, 1H), 3.51 (q,J = 6.0 Hz, 2H), 1.70 (sextet,J =J = 7.2 Hz, 2H), 0.94 (t,J = 7.2 Hz, 3H).Examples 67 11- chlorine -6- ( Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7726) : According to the general procedure -D from 4d / 4d2 mixtureStart synthesis . The polar products of the two isomers present in the crude mixture were separated by the FCC and confirmed as6r2 . Yield: 176 mg. ES-MS [M + 1]⁺ : 312.9; t_R : 3.24 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 8.53 (d,J = 8.4 Hz, 1H), 7.83 (m, 1H), 7.69-7.67 (m, 2H), 7.63 (d,J = 8.0 Hz, 1H), 7.54 (ddd,J = 8.4, 7.2, 1.2 Hz, 1H), 7.29 (ddd,J = 8.4, 6.8, 1.2 Hz, 1H), 3.50 (q,J = 6.8 Hz, 2H), 1.68 (sextet,J = 7.2 Hz, 2H), 0.93 (t,J = 7.2 Hz, 3H). Option 5 Examples 68 6,8- Dichloro -12H- Benzothieno [2,3-c] quinoline -12- ketone (4e) : Starting from 2-chlorothiophenol, the general procedure A-C was followed in 3 steps. Yield: 50% over 3 steps. ES-MS [M + 1]⁺ : 331.9; t_R : 6.90 minutes (Method-A).Examples 69 6- Amine -8- chlorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7713) : Synthesized according to the general procedure -F. Yield: 550 mg (85%). ES-MS [M + 1]⁺ : 312.9; t_R : 3.95 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.31 (d,J = 8.8, 1H), 8.41 (d,J = 7.6 Hz, 1H), 8.00 (d,J = 8.0 Hz, 1H), 7.69-7.57 (m, 3H), 7.37 (dd,J = 8.0, 6.8 Hz, 1H), 7.15 (brs, 2H).Examples 70 8- chlorine -6- ( Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7714) : Synthesized according to the general procedure -D. Yield: 630 mg (84%). ES-MS [M + 1]⁺ : 355.0; t_R : 6.57 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.30 (d,J = 8.8 Hz, 1H), 8.43 (d,J = 8.0 Hz, 1H), 8.03 (dd,J = 8.0, 1.6 Hz, 1H), 7.71-7.66 (m, 2H), 7.58 (dd,J = 8.0, 1.2 Hz, 1H), 7.37-7.32 (m, 2H), 3.54 (m, 2H), 1.71 (sextet,J = 7.2 Hz, 2H), 0.95 (t,J = 7.2 Hz, 3H).Examples 71 6- (3- Aminopropylamino )-8- chlorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7715) : Synthesized according to the general procedure -E. Yield: 400 mg (47%). ES-MS [M + 1]⁺ : 370.0; t_R : 2.34 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.28 (d,J = 8.0 Hz, 1H), 8.40 (d,J = 8.0 Hz, 1H), 8.01 (d,J = 7.6 Hz, 1H), 7.69-7.65 (m, 2H), 7.58 (t,J = 7.2 Hz, 1H), 7.34 (t,J = 7.2 Hz, 1H), 3.65 (t,J = 6.4 Hz, 2H), 2.73 (t,J = 6.4 Hz, 2H), 1.80 (quint,J = 6.4 Hz, 3H).Examples 72 8- chlorine -6- (3- (2- Hydroxyethylamino ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7716) : Synthesized according to the general procedure -D. Yield: 700 mg (74%). ES-MS [M + 1]⁺ : 414.0; t_R : 2.11 minutes (Method-A);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.26 (d,J = 8.4 Hz, 1H), 8.37 (d,J = 8.0 Hz, 1H), 7.97 (d,J = 8.0 Hz, 1H), 7.82 (brs, 1H), 7.66-7.63 (m, 2H), 7.55 (dd,J = 7.6, 7.2 Hz, 1H), 7.31 (dd,J = 8.0, 7.2 Hz, 1H), 5.00 (brs, 1H), 3.62 (t,J = 6.0 Hz, 2H), 3.53 (m, 2H), 2.71 (t,J = 6.0 Hz, 2H), 2.63 (t,J = 5.6 Hz, 2H), 1.82 (quint,J = 6.0 Hz, 2H). Option 6 Examples 73 6- chlorine -10- Trifluoromethyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (4f) : Starting from 4- (trifluoromethyl) thiophenol, the general procedure A-C was followed in 3 steps. Yield: 25% over 3 steps. ES-MS [M + 1] +: 365.8; tR: 3.83 minutes (Method-E)Examples 74 6- (3- Aminopropylamino ) -10- Trifluoromethyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (7201) : Self-stent compound according to general procedure -E4f Begin synthesis. Yield: 120 mg (36%). ES-MS [M + 1]⁺ : 403.9; t_R : 3.40 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.33 (d,J = 8.0 Hz, 1H), 8.67 (s, 1H), 8.18-8.11 (m, 2H), 7.70 (d,J = 8.4 Hz, 1H), 7.61 (t,J = 7.6 Hz, 1H), 7.38 (t,J = 7.6 Hz, 1H), 6.5 (brs, 3H), 3.66 (t,J = 6.4 Hz, 2H), 2.83 (t,J = 6.8 Hz, 2H), 1.92 (quint,J = 6.8 Hz, 2H).Examples 75 6- (3- (2- Hydroxyethylamino ) Propylamino ) -10- Trifluoromethyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (7214) : -D self scaffold compound according to general procedure4f Begin synthesis. Yield: 610 mg (89%); ES-MS [M + 1]⁺ : 447.9; t_R : 4.39 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.32 (d,J = 8.8 Hz, 1H), 8.64 (s, 1H), 8.12 (m, 2H), 7.66 (d,J = 8.4 Hz, 1H), 7.58 (dd,J = 8.4, 6.4 Hz, 1H), 7.35 (dd,J = 8.0, 7.6 Hz, 1H), 4.56 (brs, 1H), 3.62 (t,J = 6.4 Hz, 2H). 3.54 (m, 2H), 2.72 (t,J = 6.0 Hz, 2H), 2.64 (t,J = 5.2 Hz, 2H), 1.82 (quint,J = 6.0 Hz, 2H). Option 7 Examples 76 6- chlorine -10- methyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (4g) : Starting from 4-toluenethiol, synthesis was performed in 3 steps following the general procedure A-C. Yield: 48% over 3 steps. ES-MS [M + 1] +: 311.9; tR: 8.65 minutes (Method-G).Examples 77 6- (3- Aminopropylamino ) -10- methyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (7202) : Self-stent compound according to general procedure -E4g Begin synthesis. Yield: 130 mg (63%). ES-MS [M + 1]⁺ : 350.0; t_R : 2.28 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ): δ 9.34 (d,J = 8.8 Hz, 1H), 8.25 (s, 1H), 8.07 (m, 3H), 7.79 (d,J = 8.4 Hz, 1H), 7.69-7.64 (m, 2H), 7.58 (td,J = 8.4, 2.0 Hz, 1H), 7.37-7.33 (m, 2H), 3.66 (t,J = 5.6 Hz, 2H), 2.87 (t,J = 7.2 Hz, 2H), 2.47 (s, 3H; combined with residual DMSO), 2.00 (quint,J = 6.8 Hz, 2H).Examples 78 6- (3- (2- Hydroxyethylamino ) Propylamino ) -10- methyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (7215) : -D self scaffold compound according to general procedure4g Begin synthesis. Yield: 210 mg (55%). ES-MS [M + 1]⁺ : 394.0; t_R : 4.08 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.8 Hz, 1H), 8.24 (s, 1H), 7.77 (d,J = 8.0 Hz, 1H), 7.65 (m, 2H), 7.56 (t,J = 7.6 Hz, 1H), 7.34 (t,J = 7.6 Hz, 1H), 4.7 (brs, 1H), 3.63 (m, 2H), 3.56 (m, 2H), 2.75 (t,J = 5.6 Hz, 2H), 2.67 (t,J = 5.6 Hz, 2H), 1.85 (m, 2H).Examples 79 6- (2- Aminoethylamino ) -10- methyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (7231) : Self-stent compound according to general procedure -E4g Begin synthesis. Yield: 163 mg (52%). ES-MS [M + 1]⁺ : 335.9; t_R : 4.15 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.34 (d,J = 8.8 Hz, 1H), 8.25 (s, 1H), 7.82 (d,J = 8.4 Hz, 1H), 7.66 (m, 2H), 7.57 (t,J = 7.6 Hz, 1H), 7.35 (t,J = 7.6 Hz, 1H), 3.57 (t,J = 6.4 Hz, 2H), 2.87 (t,J = 6.4 Hz, 2H), 2.47 (s, 3H; combined with residual DMSO).Examples 80 6- ( Ethylamino ) -10- methyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (7232) : According to General Procedure-J Self-Scaffold Compound4f Begin synthesis. Yield: 95 mg (30%). ES-MS [M + 1]⁺ : 321.0; t_R : 6.10 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.39 (dd,J = 8.4, 1.2 Hz, 1H), 8.30 (s, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.69 (dd,J = 7.6, 6.4 Hz, 2H), 7.60 (ddd,J = 6.8, 5.6, 1.6 Hz, 1H), 7.38 (td,J = 7.2, 5.6 Hz, 1H), 7.16 (t,J = 5.2 Hz, 1H), 3.59-3.66 (m, 2H), 2.47 (s, 3H; combined with residual DMSO), 1.23-1.33 (m, 3H).Examples 81 6- ( Benzylamino ) -10- methyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (7233) : Self-stent compound according to general procedure -D4g Begin synthesis. Yield: 178 mg (55%). ES-MS [M + 1]⁺ : 382.9; t_R : 8.41 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.34 (d,J = 8.8 Hz, 1H), 8.26 (s, 1H), 7.83 (d,J = 8.0 Hz, 1H), 7.76 (t,J = 5.6 Hz, 2H), 7.70-7.62 (m, 2H), 7.55 (t,J = 8.0 Hz, 1H), 7.45 (m, 2H), 7.34 (td,J = 8.4, 1.6 Hz, 1H), 7.28 (m, 2H), 7.18 (t,J = 7.2 Hz, 1H), 4.79 (d,J = 5.6 Hz, 2H). Option 8 Examples 82 6- chlorine -10- Trifluoromethoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (4h) : Starting from 4- (trifluoromethoxy) thiophenol, the general procedure A-C was followed in 3 steps. Yield: 25% over 3 steps. ES-MS [M + 1] +: 381.9; tR: 5.90 minutes (Method-F).Examples 83 6- (3- Aminopropylamino ) -10- ( Trifluoromethoxy ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7203) : Self-stent compound according to general procedure -E4h Begin synthesis. Yield: 75 mg (23%). ES-MS [M + 1]⁺ : 419.9; t_R : 4.55 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.36 (d,J = 8.0 Hz, 1H), 8.31 (s, 1H), 8.12 (d,J = 8.8 Hz, 1H), 7.90-7.87 (m, 4H), 7.70 (d,J = 8.0 Hz, 1H), 7.62 (t,J = 7.2 Hz, 1H), 7.39 (t,J = 8.0 Hz, 1H), 3.66 (t,J = 6.4 Hz, 2H), 2.89 (t,J = 7.2 Hz, 2H), 1.99 (m, 2H). Option 9 Examples 84 6- chlorine -8- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (4i) : Starting from 2-fluorothiophenol, the general procedure A-C was followed in 3 steps. Yield: 54% over 3 steps. ES-MS [M + 1] +: 315.8; tR: 7.88 minutes (Method-G).Examples 85 6- (3- Aminopropylamino )-8- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7211) : Self-stent compound according to general procedure -E4i Begin synthesis. Yield: 145 mg (37%). ES-MS [M + 1]⁺ : 353.9; t_R : 4.01 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.31 (d,J = 8.4 Hz, 1H), 8.29 (d,J = 8.0 Hz, 1H), 7.92 (brs, 2H), 7.81 (dd,J = 9.2, 8.8 Hz, 1H), 7.74-7.70 (m, 2H), 7.61 (dd,J = 7.6, 7.2 Hz, 1H), 7.5 (brs, 1H), 7.38 (dd,J = 8.4, 6.8 Hz, 1H), 3.67 (t,J = 6.4 Hz, 2H), 2.89 (t,J = 6.8 Hz, 2H), 2.00 (quint,J = 6.4 Hz, 2H).Examples 86 8- fluorine -6- (3- (2- Hydroxyethylamino ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7224) : Self-stent compound according to general procedure -D4i Begin synthesis. Yield: 125 mg (28%). ES-MS [M + 1]⁺ : 398.0; t_R : 4.03 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.31 (d,J = 8.0 Hz, 1H), 8.74 (brs, 1H), 8.29 (d,J = 8.0 Hz, 1H), 7.82 (dd,J = 9.2, 8.8 Hz, 1H), 7.72 (m, 2H), 7.61 (t,J = 7.6 Hz, 1H), 7.5 (brs, 1H), 7.38 (t,J = 8.0 Hz, 1H), 5.26 (brs, 1H), 3.65 (m, 4H), 2.99 (m, 4H), 2.08 (m, 2H).Examples 87 6- (2- Aminoethylamino )-8- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7240) : Self-stent compound according to general procedure -E4i Begin synthesis. Yield: 102 mg (31%). ES-MS [M + 1]⁺ : 340.0; t_R : 3.98 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.30 (d,J = 8.8 Hz, 1H), 8.27 (d,J = 7.6 Hz, 1H), 7.80 (dd,J = 9.2, 8.8 Hz, 1H), 7.72-7.66 (m, 2H), 7.58 (dd,J = 7.6, 6.8 Hz, 1H), 7.35 (dd,J = 8.0, 7.2 Hz, 1H), 3.57 (t,J = 6.4 Hz, 2H), 2.86 (t,J = 6.4 Hz, 2H).Examples 88 6- ( Ethylamino )-8- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7241) : According to the General Procedure -J Self-Scaffolding Compound4i Begin synthesis. Yield: 164 mg (53%). ES-MS [M + 1]⁺ : 324.9; t_R : 5.97 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.29 (d,J = 8.0 Hz, 1H), 8.26 (d,J = 8.0 Hz, 1H), 7.79 (t,J = 8.8 Hz, 1H), 7.71-7.65 (m, 2H), 7.57 (t,J = 7.6 Hz, 1H), 7.36-7.29 (m, 2H), 3.59 (m, 2H), 1.25 (t,J = 6.8 Hz, 3H).Examples 89 6- ( Benzylamino )-8- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7242) : Self-stent compound according to general procedure -D4i Begin synthesis. Yield: 255 mg (69%). ES-MS [M + 1]⁺ : 386.9; t_R : 6.41 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.29 (d,J = 8.4 Hz, 1H), 8.27 (d,J = 8.0 Hz, 1H), 7.98 (t,J = 5.2 Hz, 1H), 7.79 (dd,J = 9.2, 8.8 Hz, 1H), 7.69 (m, 1H), 7.62 (d,J = 8.0 Hz, 1H), 7.56 (dd,J = 7.6, 6.8 Hz, 1H), 7.45 (m, 2H), 7.35 (dd,J = 7.6, 6.8 Hz, 1H), 7.28 (m, 2H), 7.17 (dd,J = 7.2, 6.8 Hz, 1H), 4.78 (d,J = 5.2 Hz, 2H). Option 10 Examples 90 6- chlorine -8- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (4j) : Starting from 2-methoxythiophenol, the general procedure A-C was followed in 3 steps. Yield: 46% over 3 steps.Examples 91 6- (3- Aminopropylamino )-8- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7212) : Self-stent compound according to general procedure -E4j Begin synthesis. Yield: 128 mg (33%); ES-MS [M + 1]⁺ : 366.0; t_R : 3.59 minutes (Method-I),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.0 Hz, 1H), 8.05 (d,J = 8.0 Hz, 1H), 7.66-7.61 (m, 2H), 7.57 (m, 1H), 7.47 (d,J = 7.6 Hz, 1H), 7.33 (dd,J = 8.0, 1.2 Hz, 1H), 4.04 (s, 3H), 3.65 (t,J = 6.8 Hz, 2H), 2.66 (t,J = 6.4 Hz, 2H), 1.76 (quint,J = 6.4 Hz, 2H).Examples 92 6- (3- (2- Hydroxyethylamino ) Propylamino )-8- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7225) : Self-stent compound according to general procedure -D4j Begin synthesis. Yield: 266 mg (71%). ES-MS [M + 1]⁺ : 410.0; t_R : 4.02 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.4 Hz, 1H), 8.04 (d,J = 7.6 Hz, 1H), 7.66-7.60 (m, 2H), 7.55 (dd,J = 8.4, 1.2 Hz, 1H), 7.45 (d,J = 7.6 Hz, 1H), 7.32 (dd,J = 8.4, 1.2 Hz, 1H), 4.51 (brs, 1H), 4.03 (s, 3H), 3.65-3.58 (m, 4H), 2.71 (t,J = 6.0 Hz, 2H), 2.63 (t,J = 6.4 Hz, 2H), 1.82 (quint,J = 6.4 Hz, 2H).Examples 93 6- (2- Aminoethylamino )-8- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7244) : Self-stent compound according to general procedure -E4j Begin synthesis. Yield: 151 mg (47%); ES-MS [M + 1]⁺ : 352.0; t_R : 4.01 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.37 (d,J = 8.4 Hz, 1H), 8.38 (s, 1H), 8.06 (d,J = 8.4 Hz, 1H), 7.71 (d,J = 8.4 Hz, 1H), 7.65 (t,J = 8.0 Hz, 1H), 7.60 (dd,J = 8.4, 7.2 Hz, 1H), 7.49 (d,J = 8.0 Hz, 1H), 7.38 (dd,J = 8.4, 8.0 Hz, 1H), 4.05 (s, 3H), 3.80 (t,J = 6.0 Hz, 2H), 3.12 (t,J = 6.0 Hz, 2H)Examples 94 6- ( Ethylamino )-8- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7245) : According to the General Procedure -J Self-Scaffolding Compound4j Begin synthesis. Yield: 196 mg (63%); ES-MS [M + 1]⁺ : 336.9; t_R : 7.04 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.0 Hz, 1H), 8.05 (d,J = 7.6 Hz, 1H), 7.66 (d,J = 8.4 Hz, 1H), 7.62 (d,J = 8.4 Hz, 1H), 7.56 (td,J = 8.0, 1.2 Hz, 1H), 7.47 (d,J = 8.0 Hz, 1H), 7.34 (td,J = 8.4, 1.2 Hz, 1H), 7.27 (brs, 1H), 4.04 (s, 3H), 3.6 (m, 2H), 1.25 (t,J = 7.2 Hz, 3H).Examples 95 6- ( Benzylamino )-8- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7246) : Self-stent compound according to general procedure -D4j Begin synthesis. Yield: 144 mg (39%); ES-MS [M + 1]⁺ : 399.0; t_R : 7.76 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (d,J = 8.4 Hz, 1H), 8.06 (d,J = 8.0 Hz, 1H), 7.93 (m, 1H), 7.64 (m, 2H), 7.56 (m, 1H), 7.49-7.45 (m, 3H), 7.34 (dd,J = 8.4, 8.0 Hz, 1H), 7.28 (m, 2H), 7.18 (m, 1H), 4.79 (d,J = 5.6 Hz, 2H), 4.05 (s, 3H).Examples 96 4- (8- Methoxy -12- Pendant oxygen -12H- Benzothieno [2,3-c] quinoline -6- base ) Hexahydropyrazine -1- Tert-butyl formate (7297) : Self-stent compound according to general procedure -D4j Begin synthesis. Yield: 260 mg (60%); ES-MS [M + 1]⁺ : 478.0; t_R : 7.11 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.55 (d,J = 8.8 Hz, 1H), 8.08 (d,J = 8.4 Hz, 1H), 7.94 (d,J = 8.4 Hz, 1H), 7.75 (dd,J = 8.0, 7.2 Hz, 1H), 7.67-7.61 (m, 2H), 7.48 (d,J = 8.0 Hz, 1H), 4.05 (s, 3H), 3.61 (brs, 4H), 3.28 (brs, 4H), 1.43 (s, 9H).Examples 97 8- Methoxy -6- ( Hexahydropyrazine -1- base ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7247) : Used in the first stage according to the general procedure -FN -Boc hexahydropyrazine was synthesized in place of 4-methoxybenzylamine. Yield: 206 mg (98%); ES-MS [M + 1]⁺ : 378.0; t_R : 4.32 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.55 (d,J = 8.4 Hz, 1H), 8.99 (brs, 1H), 8.07 (d,J = 8.0 Hz, 1H), 7.95 (d,J = 8.0 Hz, 1H), 7.77 (m, 1H), 7.67-7.61 (m, 2H), 7.49 (d,J = 8.0 Hz, 1H), 4.04 (s, 3H), 3.53 (m, 4H), 3.40 (m, 4H). Option 11 Examples 98 6,8- Dichloro -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (4k) : Starting from 2-chloro-4-fluorobenzenethiol, the general procedure A-C was followed in 3 steps. Yield: 40% over 3 steps. ES-MS [M + H] +: 351.8; tR: 9.41 minutes (Method-E).Examples 99 6- (3- Aminopropylamino )-8- chlorine -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7213) : Self-stent compound according to general procedure -E4k Begin synthesis. Yield: 108 mg (33%); ES-MS [M + 1]⁺ : 388.0; t_R : 4.45 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (dd,J = 8.8, 1.2 Hz, 1H), 8.24-8.19 (m, 2H), 7.77 (t,J = 4.8 Hz, 1H), 7.73-7.70 (m, 1H), 7.65-7.61 (m, 1H), 7.43-7.38 (m, 1H), 3.74-3.67 (m, 2H), 3.33 (m, 2H; and HOD signal combined), 2.08-1.97 (m, 2H).Examples 100 8- chlorine -10- fluorine -6- (3- (2- Hydroxyethylamino ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7226) : Self-stent compound according to general procedure -D4k Begin synthesis. Yield: 172 mg (40%). ES-MS [M + 1]⁺ : 431.9; t_R : 4.42 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.31 (d,J = 8.4 Hz, 1H), 8.72 (brs, 1H), 8.21-8.15 (m, 2H), 7.70 (d,J = 8.0 Hz, 1H), 7.61 (t,J = 7.6 Hz, 1H), 7.53 (brs, 1H), 7.38 (t,J = 7.6 Hz, 1H), 5.25 (brs, 1H), 3.65 (m, 4H), 3.01 (m, 4H), 2.08 (m, 2H).Examples 101 6- (2- Aminoethylamino )-8- chlorine -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7248) : Self-stent compound according to general procedure -E4k Begin synthesis. Yield: 100 mg (31%); ES-MS [M + 1]⁺ : 374.0; t_R : 4.38 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.33 (d,J = 8.4 Hz, 1H), 8.21 (m, 2H), 7.72 (td,J = 6.8, 1.6 Hz, 1H), 7.62 (td,J = 8.0, 6.8 Hz, 1H), 7.39 (td,J = 6.8, 2.8 Hz, 1H), 3.62 (t,J = 6.8 Hz, 2H), 2.91 (t,J = 6.4 Hz, 2H).Examples 102 8- chlorine -6- ( Ethylamino ) -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7249) : According to the General Procedure -J Self-Scaffolding Compound4k Begin synthesis. Yield: 87 mg (28%). ES-MS [M + 1]⁺ : 358.8; t_R : 6.88 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.27 (d,J = 8.8 Hz, 1H), 8.13 (m, 2H), 7.65 (d,J = 8.4 Hz, 1H), 7.58 (m, 1H), 7.36-7.30 (m, 2H), 3.59 (m, 2H), 1.26 (t,J = 6.8 Hz, 3H).Examples 103 6- ( Benzylamino )-8- chlorine -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7250) : Self-stent compound according to general procedure -D4k Begin synthesis. Yield: 175 mg (48%). ES-MS [M + 1]⁺ : 420.9; t_R : 7.19 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.23 (d,J = 8.4 Hz, 1H), 8.15 (m, 2H), 7.99 (m, 1H), 7.61 (d,J = 8.0 Hz, 1H), 7.56 (m, 1H), 7.45 (m, 2H), 7.34 (t,J = 7.2 Hz, 1H), 7.28 (m, 2H), 7.19 (m, 1H), 4.78 (d,J = 4.4 Hz, 2H). Scheme 12 Examples 104 6- chlorine -8,10- Difluoro -12H- Benzothieno [2,3-c] quinoline -12- ketone (4l) : Starting from 2,4-difluorobenzenethiol, synthesis was performed in 3 steps following the general procedure A-C. Yield: 13% over 3 steps. ES-MS [M + H] +: 333.9; tR: 8.25 minutes (Method-G).Examples 105 6- (3- Aminopropylamino ) -8,10- Difluoro -12H- Benzothieno [2,3-c] quinoline -12- ketone (7252) : Self-stent compound according to general procedure -E4l Begin synthesis. Yield: 255 mg (76%). ES-MS [M + 1]⁺ : 372.1; t_R : 4.27 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.34 (d,J = 8.4 Hz, 1H), 8.12-8.00 (m, 2H), 7.96-7.74 (m, 2H), 7.69-7.60 (m, 1H), 7.41 (dd,J = 7.2, 6.8 Hz, 1H), 3.69 (t,J = 6.4Hz, 2H), 2.91 (t,J = 7.2 Hz, 2H), 2.02 (m, 2H).Examples 106 8,10- Difluoro -6- (3- (2- Hydroxyethylamino ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7253) : Self-stent compound according to general procedure -D4l Begin synthesis. Yield: 130 mg (42%). ES-MS [M + 1]⁺ : 416.1; t_R : 4.23 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.36 (d,J = 8.8 Hz, 1H), 8.85 (brs, 1H), 8.03-8.14 (m, 2H), 7.76 (d,J = 7.6 Hz, 1H), 7.65 (td,J = 7.2, 6.8 Hz, 1H), 7.57 (m, 1H), 7.41 (dd,J = 8.4, 6.8 Hz, 1H), 5.28 (t,J = 5.2 Hz, 1H), 3.67 (m, 4H), 2.99-3.06 (m, 4H), 2.07-2.14 (m, 2H).Examples 107 6- (2- Aminoethylamino ) -8,10- Difluoro -12H- Benzothieno [2,3-c] quinoline -12- ketone (7254) : Self-stent compound according to general procedure -E4l Begin synthesis. Yield: 25 mg (8%). ES-MS [M + 1]⁺ : 358.0; t_R : 4.26 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.36 (d,J = 8.4 Hz, 1H), 8.05-7.98 (m, 2H), 7.70 (d,J = 8.0 Hz, 1H), 7.62 (ddd,J = 8.0, 6.8, 1.2 Hz, 1H), 7.39 (ddd,J = 8.4, 6.8, 1.6 Hz, 1H), 3.61 (t,J = 9.6 Hz, 2H), 2.90 (t,J = 9.6 Hz, 2H).Examples 108 6- ( Ethylamino ) -8,10- Difluoro -12H- Benzothieno [2,3-c] quinoline -12- ketone (7255) : According to the General Procedure -J Self-Scaffolding Compound4l Begin synthesis. Yield: 128 mg (42%). ES-MS [M + 1]⁺ : 343.0; t_R : 6.27 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.32 (dd,J = 8.4, 0.8 Hz, 1H), 8.05 (m, 2H), 7.69 (dd,J = 8.4, 1.2 Hz, 1H), 7.61 (td,J = 6.8, 1.2 Hz, 1H), 7.39 (dd,J = 6.8, 1.2 Hz, 1H), 7.34 (t,J = 5.2 Hz, 1H), 3.62 (m, 2H), 1.27 (t,J = 6.0 Hz, 3H).Examples 109 6- ( Benzylamino ) -8,10- Difluoro -12H- Benzothieno [2,3-c] quinoline -12- ketone (7256) : Self-stent compound according to general procedure -D4l Begin synthesis. Yield: 95 mg (52%). ES-MS [M + 1]⁺ : 405.0; t_R : 6.62 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.34 (dd,J = 8.4, 1.2 Hz, 1H), 8.05 (m, 3H), 7.67 (dd,J = 8.4, 1.2 Hz, 1H), 7.61 (td,J = 6.8, 1.2 Hz, 1H), 7.48 (dd,J = 8.4, 1.2 Hz, 2H), 7.39 (td,J = 6.8, 1.6 Hz, 1H), 7.31 (t,J = 7.2 Hz, 2H), 7.21 (t,J = 7.2 Hz, 1H), 4.87 (d,J = 5.6 Hz, 2H). Scheme 13 Examples 110 6- chlorine -10- fluorine -4- methyl -12H- Benzothieno [2,3-c] quinoline -12- ketone (4m) : 7-methyl isatin and compounds in 2 steps2a Started the general procedure B-C synthesis. Yield: 51% over 2 steps. ES-MS [M + 1] +: 329.9; tR: 4.19 minutes (Method-K). Scheme 14 Examples 111 2,6- Dichloro -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (4n) : 5-Chloroisatin and Compounds in 2 Steps2a Started the general procedure B-C synthesis. Yield: 40% over 2 steps. ES-MS [M + 1] +: 349.8; tR: 9.39 minutes (Method-G).Examples 112 6-((3- Aminopropyl ) Amine )-2- chlorine -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7403) : -D self scaffold compound according to general procedure4n Begin synthesis. Yield: 150 mg (46%). ES-MS [M + 1]⁺ : 387.9; t_R : 3.44 minutes (Method-F),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.42 (d,J = 2.4 Hz, 1H), 8.14-8.10 (m, 3H), 8.01 (dd,J = 8.8, 4.8 Hz, 1H), 7.77 (ddd,J = 8.8, 8.4, 2.8 Hz, 1H), 7.65 (d,J = 8.8 Hz, 1H), 7.59-7.57 (m, 2H), 3.63 (m, 2H), 2.87 (t,J = 7.2 Hz, 2H), 2.0 (m, 2H).Examples 113 2- chlorine -10- fluorine -6- (3- (2- Hydroxyethylamino ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7406) : Self-stent compound according to general procedure -D4n Begin synthesis. Yield: 126 mg (34%). ES-MS [M + 1]⁺ : 431.9; t_R : 4.48 minutes (Method-G);¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.46 (d,J = 2.4 Hz, 1H), 8.8 (brs, 1H), 8.17 (dd,J = 9.6, 2.8 Hz, 1H), 8.05 (dd,J = 8.8, 4.8 Hz, 1H), 7.80 (td,J = 8.8, 2.8 Hz, 1H), 7.69 (d,J = 8.8 Hz, 1H), 7.61 (dd,J = 8.8, 2.4 Hz, 1H), 7.59 (brs, 1H), 5.24 (m, 1H), 3.65 (m, 4H), 3.01-2.94 (m, 4H), 2.07 (m, 2H).Examples 114 6- ( Benzylamino )-2- chlorine -10- fluorine -12H- Benzothieno [2,3-c] quinoline -12- ketone (7416) : Self-stent compound according to general procedure -D4n Begin synthesis. Yield: 259 mg (71%), ES-MS [M + 1]⁺ : 421.0, t_R : 7.42 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.48 (d,J = 2.0 Hz, 1H), 9.05 (d,J = 2.0 Hz, 1H), 9.05 (d,J = 2.8 Hz, 1H), 9.05 (d,J = 2.8 Hz, 1H), 9.05 (d,J = 2.8 Hz, 1H). Scheme 15 Examples 115 6-Chloro-2,10-difluoro-12H-benzothieno [2,3-c] quinolin-12-one (4o): 2-fluoroisatin and compounds in 2 steps2a Started the general procedure B-C synthesis. Yield: 53% over 2 steps. ES-MS [M + 1] +: 333.8; tR: 7.90 minutes (Method-G).Examples 116 6- (3- Aminopropylamino ) -2,10- Difluoro -12H- Benzothieno [2,3-c] quinoline -12- ketone (7402) : Self-stent compound according to general procedure -E4o Begin synthesis. Yield: 200 mg (60%), ES-MS [M + 1]⁺ : 372.0, t_R : 4.21 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.18 (dd,J = 8.8, 2.8 Hz, 1H), 8.20 (brs, 2H), 8.15 (dd,J = 9.6, 2.8 Hz, 1H), 8.04 (dd,J = 9.2, 8.8 Hz, 1H), 7.79 (m, 1H), 7.72 (dd,J = 9.2, 5.2 Hz, 1H), 7.50 (m, 1H), 7.44 (m, 1H), 3.643 (m, 2H), 2.86 (m, 2H), 2.02 (m, 2H).Examples 117 2,10- Difluoro -6- (3- (2- Hydroxyethylamino ) Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7408) : Self-stent compound according to general procedure -D4o Begin synthesis. Yield: 190 mg (51%), ES-MS [M + 1]⁺ : 416.0, t_R : 4.20 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.18 (dd,J = 12.8, 3.2 Hz, 1H), 8.8 (brs, 1H), 8.15 (dd,J = 10.0, 2.8 Hz, 1H), 8.04 (dd,J = 8.8, 5.2 Hz, 1H), 7.79 (ddd,J = 8.8, 8.4, 2.8 Hz, 1H), 7.73 (dd,J = 8.8, 6 Hz, 1H), 7.53-7.45 (m, 2H), 5.25 (brs, 1H), 3.64 (m, 4H), 3.0-2.93 (m, 4H), 2.01 (m, 2H).Examples 118 6- (2- Aminoethylamino ) -2,10- Difluoro -12H- Benzothieno [2,3-c] quinoline -12- ketone (7422) : Self-stent compound according to general procedure -E4o Begin synthesis. Yield: 102 mg (31%), ES-MS [M + 1]⁺ : 357.9, t_R : 4.16 minutes (Method-F),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.20 (dd,J = 12.8, 2.8 Hz, 1H), 8.18 (ddd,J = 10.0, 9.6, 2.8 Hz, 1H), 8.09-8.05 (m, 4H), 7.83-7.75 (m, 2H), 7.54 (td,J = 8.8, 2.8 Hz, 1H), 8.04 (dd,J = 8.8, 5.2 Hz, 1H), 7.42 (t,J = 4.8 Hz, 1H), 3.81 (m, 2H), 3.16 (m, 2H).Examples 119 6- ( Benzylamino ) -2,10- Difluoro -12H- Benzothieno [2,3-c] quinoline -12- ketone (7424) : Self-stent compound according to general procedure -D4o Begin synthesis. Yield: 149 mg (41%), ES-MS [M + 1]⁺ : 404.9, t_R : 6.49 minutes (Method-J),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.18 (dd,J = 12.8, 2.8 Hz, 1H), 8.16 (ddd,J = 10.0, 9.6, 2.8 Hz, 1H), 8.06 (m, 1H), 7.82-7.76 (m, 2H), 7.66 (dd,J = 8.8, 6 Hz, 1H), 7.49-7.43 (m, 3H), 7.28 (m, 2H), 7.18 (dd,J = 7.6, 7.2 Hz, 1H), 4.77 (d,J = 5.6 Hz, 2H).Examples 120 4- (2,10- Difluoro -12- Pendant oxygen -12H- Benzothieno [2,3-c] quinoline -6- base ) Hexahydropyrazine -1- Tert-butyl formate (7495) : Self-stent compound according to general procedure -D4o Begin synthesis. Yield: 300 mg (69%), ES-MS [M + 1]⁺ : 484.0, t_R : 7.77 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.35 (dd,J = 12.8, 2.8 Hz), 8.18-8.11 (m, 2H), 7.99 (dd,J = 9.2, 6 Hz), 7.79 (m, 1H), 7.67 (m, 1H), 3.62 (m, 4H), 3.25 (m, 4H), 1.43 (s, 9H).Examples 121 2,10- Difluoro -6- ( Hexahydropyrazine -1- base ) -12H- Benzothieno [2,3-c] quinoline -12- ketone (7425) : Synthesis according to general procedure -F starting from 1-Boc hexahydropyrazine instead of 4-methoxybenzylamine in step -1. Yield: 300 mg (69%), ES-MS [M + 1]⁺ : 383.9, t_R : 4.66 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.32 (dd,J = 12.8, 2.8 Hz), 8.15-8.09 (m, 2H), 7.99 (dd,J = 9.2, 6 Hz), 7.78 (td,J = 8.4, 2.8 Hz, 1H), 7.61 (td,J = 8.8, 2.8 Hz, 1H), 3.35 (m, 4H), 3.20 (m, 4H). Scheme 16 Examples 122 6- chlorine -10- fluorine -2- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (4p) : 5-methoxyisatin and compounds in 2 steps2a Started the general procedure B-C synthesis. Yield: 30% over 2 steps. ES-MS [M + 1] +: 345.8; tR: 8.04 minutes (Method-G).Examples 123 10- fluorine -6- (3- (2- Hydroxyethylamino ) Propylamino )-2- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7407) : Self-stent compound according to general procedure -D4p Begin synthesis. Yield: 135 mg (44%), ES-MS [M + 1]⁺ : 428.0, t_R : 4.09 minutes (Method-G),¹ H NMR (400 MHz, DMSO-d₆ ): δ 9.02 (d,J = 2.8 Hz, 1H), 8.88 (brs, 1H), 8.17 (dd,J = 9.6, 2.8 Hz, 1H), 8.02 (dd,J = 9.2, 5.2 Hz, 1H), 7.77 (td,J = 8.8, 2.8 Hz, 1H), 7.66 (d,J = 8.8 Hz, 1H), 7.29 (dd,J = 9.2, 2.8 Hz, 1H), 7.11 (t,J = 4.8 Hz, 1H), 5.25 (brs, 1H), 3.85 (s, 3H), 3.66-3.59 (m, 4H), 3.00-2.64 (m, 4H), 2.10-2.05 (m, 2H).Examples 124 6- ( Benzylamino ) -10- fluorine -2- Methoxy -12H- Benzothieno [2,3-c] quinoline -12- ketone (7420) : Self-stent compound according to general procedure -D4p Begin synthesis. Yield: 37 mg (10%), ES-MS [M + 1]⁺ : 417.0, t_R : 7.87 minutes (Method-E),¹ H NMR (400 MHz, DMSO-d₆ ):δ 9.05 (d,J = 2.8 Hz, 1H), 8.21 (dd, J = 9.6, 2.8 Hz, 1H), 8.08 (dd,J = 8.8, 4.8 Hz, 1H), 7.80 (td,J = 8.4, 2.8 Hz, 1H), 7.62 (d,J = 8.8 Hz, 1H), 7.54 (t,J = 5.6 Hz, 1H), 7.47 (d, J = 7.2Hz, 2H), 7.26-7.31 (m, 3H), 7.21 (t,J = 7.2 Hz, 1H), 4.78 (d,J = 5.6 Hz, 2H), 3.87 (s, 3H). Scheme 17Scheme 18Scheme 19Option 20Scheme 21Scheme 22Scheme 23Scheme 24Option 25Scheme 26Scheme 27Scheme 28Scheme 29Scheme 30Scheme 31 Examples 124 6,10- Dichloro -12H- Benzothieno [2,3-c] quinoline -12- ketone 7,7- Dioxide (5a) : Self-stent compound according to general procedure -L4a Begin synthesis. Yield: 480 mg (83%), ES-MS [M + 1]⁺ : 363.8, t_R : 4.2 minutes (Method-E),¹ H NMR (400 MHz, TFA-d):δ 9.07 (d,J = 7.6 Hz, 1H), 8.38 (m, 2H), 8.32-8.27 (m, 2H), 8.1 (m, 2H).¹³ C NMR (100 MHz, CDCl₃ ): 121.66, 125.37, 127.59, 128.51, 129.33, 130.85, 131.91, 132.27, 133.62, 135.23, 137.63, 138.46, 140.61, 143.04, 149.22, 179.89.Examples 125 6- Amine -10- chlorine -12H- Benzothieno [2,3-c] quinoline -12- ketone 7,7- Dioxide (7001) : At 40 ° C according to the general procedure -F5a Started by using CHCl₃ Synthesized as a solvent instead of DMSO. Yield: 310 mg (63%). ES-MS [M + 1]⁺ : 344.9; t_R : 3.68 minutes (Method-A),¹ H NMR (400 MHz, CDCl₃ ):δ 8.58 (d,J = 8.8 Hz, 1H), 8.12 (s, 1H), 8.07 (d,J = 8.4 Hz, 1H), 7.81 (d,J = 8.4 Hz, 1H), 7.73-7.67 (m, 2H), 7.44 (dd,J = 7.6, 7.2 Hz, 1H), 6.12 (brs, 2H).Examples 126 10- chlorine -6- ( Propylamino ) -12H- Benzothieno [2,3-c] quinoline -12- ketone 7,7- Dioxide (7002) : will5a (1.0 equivalent), propylamine (5.0 equivalent) in CHCl₃ The mixture (about 4-5 times the volume) was stirred at RT for 24 hours. After completion of the reaction is monitored by TLC, the solvent is concentrated. The crude product was purified by FCC to obtain the target compound as an orange-red solid. Yield: 130 mg (61%). ES-MS [M + 1]⁺ : 387.0; t_R : 5.63 minutes (Method-A),¹ H NMR (400 MHz, CDCl₃ ):δ 8.48 (d,J = 8.8 Hz, 1H), 8.09 (d,J = 1.6 Hz, 1H), 8.04 (d,J = 8.4 Hz, 1H), 7.79 (dd,J = 8.0, 2.0 Hz, 1H), 7.73 (d,J = 8.4 Hz, 1H), 7.66 (dd,J = 7.6, 7.2 Hz, 1H), 7.35 (dd,J = 8.0, 7.2 Hz, 1H), 6.89 (brs, 1H). 3.65 (m, 2H), 1.77 (sextet,J = 7.2 Hz, 2H), 1.06 (t,J = 7.2 Hz, 3H).Examples 127 6-((3- Aminopropyl ) Amine ) -10- chlorine -12 H- Benzothieno [2,3- c ] quinoline -12- ketone 7,7- Dioxide (7003) : To RT7704 (1.0 equivalent) and TFA (about 30 times the volume) in a stirred solution₂ O₂ The solution (about 7 volumes), and the mixture was further stirred at the same temperature for 1 hour. After completion of the reaction is monitored by LCMS, the solvent is concentrated. The resulting residue was quenched with ice cold water and saturated NaHCO₃ The solution (pH about 8) was basified and diluted with EtOAc (100 ml). The precipitated product was filtered; washed with water and dried under vacuum to give the target compound as an orange-red solid in almost pure form. Yield: 85 mg (31%). ES-MS [M + 1]⁺ : 401.9; t_R : 2.16 minutes (Method-A),¹ H NMR (400 MHz, CDCl₃ ): (Poor peak resolution observed; 4 signals corresponding to the two methylene protons)δ 8.37 (d,J = 7.6 Hz, 1H), 8.17-8.08 (brm, 3H), 7.72 (brm, 1H), 7.64 (brm, 1H), 7.39 (brm, 1H), 7.23 (brm, 1H), 6.8 (brm, 1H) , 3.63 (m, 2H), 3.03 (m, 1H), 2.66 (t,J = 6.0 Hz, 1H), 1.74 (t,J = 6.0 Hz, 2H).Examples 128 10- chlorine -6-((3-((2- Hydroxyethyl ) Amine ) Propyl ) Amine ) -12H- Benzothieno [2,3-c] quinoline -12- ketone 7,7- Dioxide (7004) : will5a (1.0 equivalent), 3-((2-hydroxyethyl) amino) propyl) amine (5.0 equivalent) in CHCl₃ (Approximately 4-5 volumes) the mixture was stirred at RT for 24 hours. After completion of the reaction is monitored by TLC, the solvent is concentrated. The crude product was purified by FCC to obtain the target compound as an orange-red solid. Yield: 105 mg (9%). ES-MS [M + 1]⁺ : 446.0; t_R : 2.26 minutes (Method-A),¹ H NMR (400 MHz, DMSO-d₆ ):δ 8.42 (d,J = 8.6 Hz, 1H), 8.30 (m, 1H), 8.23 (s, 1H), 8.2 (d,J = 6.8 Hz, 1H), 8.12 (d,J = 8.4 Hz, 1H), 7.77 (m, 1H), 7.68 (d,J = 8.5 Hz, 1H), 7.45 (t,J = 7.0 Hz, 1H), 7.33 (brs, 1H), 5.2 (brs, 1H), 3.71 (d,J = 5.6 Hz, 2H), 3.63 (d,J = 4.6 Hz, 2H), 3.03-2.98 (m, 4H), 2.04 (m, 2H). Biological analysis In freshly prepared basic reaction buffer (20 mM Hepes (pH 7.5), 10 mM MgCl₂ , 1 mM EGTA, 0.02% Brij35, 0.02 mg / ml BSA, 0.1 mM Na₃ VO₄ , 2 mM DTT, 1% DMSO). Any desired cofactors are delivered to the substrate solution described above. The indicated kinase was delivered to the substrate solution and mixed gently. Test compounds in DMSO were added to the kinase reaction mixture by Acoustic technology (Echo550; nanoliter range) and incubated for 20 minutes at room temperature. 33P-ATP (specific activity 10 uM) was delivered to the reaction mixture to initiate the reaction. The kinase reaction was incubated for 2 hours at room temperature. The reaction was spotted on P81 ion exchange paper. Kinase activity was detected by filtration binding. Inhibition of FLT3 by 4-quinolinone derivatives (A: <51 nM; B: 51-200 nM; C: 201-500 nM; D: 501-1000 nM; E:> 1 uM; N / A: Not applicable)

Claims (13)

A compound having the following formula (I-1), (I-2), (I-3) or (I-4), or , Or a solvate, prodrug, stereoisomer, isomer, or pharmaceutically acceptable salt thereof, wherein Y is [P] n, and P is -CH-, -N-, or -O-; X is [Q] n, where Q is -CH _2- , -N-, -O-, -S-, -SO ₂ -or -N-alkyl; n is 0 or 1; R ₁ represents mono-, Di-, tri-, or tetra-substituted and is selected from halogen, -OH, -NH ₂ , -NO ₂ , -CN, alkyl, alkenyl, haloalkyl, -NHR _a , N (R _b ) ₂ , -OR _a , 3-membered cycloalkyl, 4-membered cycloalkyl, 5-membered cycloalkyl or 6-membered cycloalkyl, 3-, 1 or 2 heteroatoms selected from N, O, and S 4-, 5- or 6-heterocycloalkyl, aryl or heteroaryl; R _a is H, alkyl, alkenyl, halogen, hydroxyalkyl, -OH, -NO ₂ or phenyl; R _b is Alkyl, alkenyl or halogen; R ₂ is -NR _d R _e- , -O-alkyl, -C (= O) -5 or 6-membered aryl or -C (= O)-5 or 6-membered Aryl; _Rd OH, alkyl, alkenyl, aryl, heteroaryl, heteroalkenyl, -alkylene-NR _a R _e , -alkylene -N (R _b ) ₂ , -alkylene group -OR _c, - alkylene-5 or 6-membered aryl, - alkylene-5 or 6 membered heteroaryl group containing at least one N or the 5 or 6-membered heterocycloalkyl or heteroaryl; R _e H, alkyl, alkenyl or aryl group; or R _d R _e with N to form 3-8 heterocycloalkyl or heteroaryl ring, which is optionally substituted with C ₁ -C ₃ alkyl, C ₁ -C ₃ alkylene-phenyl, third butyloxycarbonyl substituted or N substituted, R _c is H, alkyl, alkenyl, halogen or phenyl; R ₃ is H, alkyl, alkenyl, halogen or CN, NH ₂ or NO ₂ ; wherein the alkyl or alkenyl group is unbranched or branched, unsubstituted or substituted with halogen, hydroxyl, amino or nitro; and wherein the cycloalkyl or heterocycloalkyl Unsubstituted or substituted with halogen, -OH, -NH ₂ , -NO ₂ , -CN, alkyl, alkenyl, -NHR _a , N (R _b ) ₂ or -OR _a ; provided that P is -CH- When n is 1, R _{1 is} not Cl. As in the compound of claim 1, Q is -S- and n is 1. As in the compound of claim 1, P is -C- or -N- and n is 1. As the compound of claim 1, R ₁ is CN, F, Cl, -OC _1-4 alkyl, C _1-4 alkyl, or halo C _1-4 alkyl. As the compound of claim 1, R ₂ is -NH-C _1-3 alkylene-NHR _a , -NH-C _1-3 alkylene-NH ₂ , -NH-C _1-3 alkylene-OH , -NH-C _1-3 alkylene-NHC _1-4 alkyl OH, -C _1-3 alkylene-5 or 6-membered aryl, -C _1-3 alkylene-5 or 6-membered Aryl. As in the compound of claim 1, R ₃ is H. The compound of claim 1 is selected from the group consisting of: Or a solvate, prodrug, stereoisomer, mirror isomer, or pharmaceutically acceptable salt thereof. A pharmaceutical composition comprising the compound according to any one of claims 1 to 7 or a pharmaceutically acceptable ester, salt or prodrug thereof, and a pharmaceutically acceptable carrier. A method of inhibiting FLT3 comprising contacting a cell with a compound as claimed in any one of claims 1 to 7. A method of treating or preventing a disease associated with FLT3 inhibition in an individual, comprising administering an effective amount of a compound according to any one of claims 1 to 7. The method of claim 10, wherein the disease associated with FLT3 inhibition is cancer. The method according to claim 11, wherein the cancer is invasive breast cancer, adenocarcinoma, lung cancer (non-small cell, squamous cell carcinoma, adenocarcinoma and large cell lung cancer), liver cancer, colorectal cancer, brain cancer, head and neck cancer (e.g. Nerve / glioblastoma), breast cancer, ovarian cancer, bladder transitional cell cancer, prostate cancer, oral squamous cell carcinoma, osteosarcoma, adrenocortical cancer, gastrointestinal tumors including colorectal cancer, such as gallbladder cancer (gallbladder carcinoma (GBC) and other bile duct cancer, bladder cancer, esophageal cancer, gastric cancer, cervical cancer, salivary adenocarcinoma, diarrhea, benign neoplasm, ductal carcinoma in situ, paronychia, bile duct cancer, kidney cancer, pancreatic cancer, marrow Blastoma, glioblastoma; breast duct type, HER2-positive and triple-negative breast tumors; hematological malignancy or leukemia (acute myelogenous leukemia AML), B-precursor acute lymphoblastic leukemia (acute lymphoblastic leukemia; ALL), a small portion of T cell ALL, and chronic myelogenous leukemia (CML)). The method of claim 11, wherein the cancer is leukemia.