77156-85-5

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate is used as a building block for the development of new drugs due to its potential biological activities. It has shown promise as an antitumor agent, making it a valuable component in the synthesis of anticancer drugs. Its unique structure allows for the design of novel therapeutic agents with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate serves as a key intermediate for the synthesis of pesticides. Its chloro and methoxy groups contribute to its pesticidal properties, making it a useful component in the development of new and effective agrochemicals for crop protection and disease control.
Used in Organic Synthesis:
Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate is used as a versatile intermediate in the preparation of various organic compounds. Its ester functionality allows for further chemical modifications and reactions, enabling the synthesis of a wide range of organic molecules with diverse applications in different industries, such as pharmaceuticals, materials science, and specialty chemicals.

InChI:InChI=1/C13H12ClNO3/c1-3-18-13(16)10-7-15-11-6-8(17-2)4-5-9(11)12(10)14/h4-7H,3H2,1-2H3

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 536-90-3 m-Anisidine 
• 71083-05-1 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 63463-15-0 ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate 
• 56881-19-7 Diethyl 2-<(3-methoxyphenylamino)methylene>malonate 

Downstream Products

• 852062-08-9 4-chloro-7-methoxyquinoline-3-carboxylic acid 
• 71082-46-7 ethyl 7-methoxy quinoline-3-carboxylate 
• 1373766-78-9 6-(dimethylamino)hexyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373766-77-8 3-(dimethylamino)propyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373766-76-7 2-(dimethylamino)ethyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373766-75-6 2-morpholinoethyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373766-74-5 2-morpholinoethyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373767-04-4 ethyl 2-(3-fluoro-5-methoxyphenyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 1373767-03-3 ethyl 2-(3,5-dimethoxyphenyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate 

Relevant academic research and scientific papers

OXADIAZOLE INHIBITORS OF HIPK2 FOR TREATING KIDNEY FIBROSIS

Compounds that are selective inhibitors of Smad3 activation are disclosed. The compounds have the structure (I) in which Z is an oxadiazole. The compounds disclosed are useful in treatment of fibrotic disease, particularly renal fibrosis, and similar dise

Design and Synthesis of Novel Deuterated Ligands Functionally Selective for the γ-Aminobutyric Acid Type A Receptor (GABAAR) α6 Subtype with Improved Metabolic Stability and Enhanced Bioavailability

Recent reports indicate that α6β2/3γ2 GABAAR selective ligands may be important for the treatment of trigeminal activation-related pain and neuropsychiatric disorders with sensori-motor gating deficits. Based on 3 functionally α6β2/3γ2 GABAAR selective pyrazoloquinolinones, 42 novel analogs were synthesized, and their in vitro metabolic stability and cytotoxicity as well as their in vivo pharmacokinetics, basic behavioral pharmacology, and effects on locomotion were investigated. Incorporation of deuterium into the methoxy substituents of the ligands increased their duration of action via improved metabolic stability and bioavailability, while their selectivity for the GABAAR α6 subtype was retained. 8b was identified as the lead compound with a substantially improved pharmacokinetic profile. The ligands allosterically modulated diazepam insensitive α6β2/3γ2 GABAARs and were functionally silent at diazepam sensitive α1β2/3γ2 GABAARs, thus no sedation was detected. In addition, these analogs were not cytotoxic, which render them interesting candidates for treatment of CNS disorders mediated by GABAAR α6β2/3γ2 subtypes.

LIGANDS SELECTIVE TO ALPHA 6 SUBUNIT-CONTAINING GABAA RECEPTORS ANS THEIR METHODS OF USE

Provided herein are novel pyrazoloquinolinone compounds and method of using such compounds to treat disorders such as neuropsychiatric disorders with sensorimotor gating deficits, such as schizophrenia, tic disorders, attention deficit hyperactivity disorder, obsessive compulsive disorder, panic disorder, Huntington's disease and nocturnal enuresis;depression; temporomandibular myofascial pain; disorders of trigeminal nerve, such as trigeminal neuralgia and trigeminal neuropathy; migraine; and tinnitus.

SUBSTITUTED NAPHTHYRIDINE AND QUINOLINE COMPOUNDS AS MAO INHIBITORS

The invention provides a chemical entity of Formula (I) wherein R1, R2, R3, Y, and n have any of the values described herein and compositions comprising such chemical entities; methods of making them; and their use in a wi

Lead optimization of 3-carboxyl-4(1 H)-quinolones to deliver orally bioavailable antimalarials

Malaria is a protozoal parasitic disease that is widespread in tropical and subtropical regions of Africa, Asia, and the Americas and causes more than 800,000 deaths per year. The continuing emergence of multidrug-resistant Plasmodium falciparum drives the ongoing need for the development of new and effective antimalarial drugs. Our previous work has explored the preliminary structural optimization of 4(1H)-quinolone ester derivatives, a new series of antimalarials related to the endochins. Herein, we report the lead optimization of 4(1H)-quinolones with a focus on improving both antimalarial potency and bioavailability. These studies led to the development of orally efficacious antimalarials including quinolone analogue 20g, a promising candidate for further optimization.

Synthesis and structure-activity relationships of antimalarial 4-oxo-3-carboxyl quinolones

Malaria is endemic in tropical and subtropical regions of Africa, Asia, and the Americas. The increasing prevalence of multi-drug-resistant Plasmodium falciparum drives the ongoing need for the development of new antimalarial drugs. In this light, novel s

THERAPEUTIC PYRAZOLOQUINOLINE UREA DERIVATIVES

The invention provides a novel chemical series of formula I, as well as methods of use thereof for binding to the benzodiazepine site of the GABAA receptor and modulating GABAA, and use of the compound of formula I for the treatment

SUBSTITUTED PYRAZOLES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF USE

The present invention relates to substituted pyrazoles, compositions containing such compounds and methods of treatment. The compounds are glucagon receptor antagonists and thus are useful for treating, preventing or delaying the onset of type 2 diabetes

SUBSTITUTED NITROGEN-CONTAINING SIX-MEMBERED AMINO-HETEROCYCLES AS VANILLOID-1 RECEPTOR ANTAGONISTS FOR TREATING PAIN

The present invention provides a compound of formula (I): Y-J-NH-Z wherein: Y is a quinoline or isoquinoline optionally substituted with one or two substituents independently chosen from hydroxy, halogen, haloC1-4alkyl, C1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, nitro and amino; J is pyridine, pyridazine, pyrazine, pyrimidine or triazine optionally substituted with one or two substituents independently chosen from hydroxy, halogen, haloC1-4alkyl, C1-4alkyl, C3-5cycloalkyl, C1-4alkoxy, hydroxyC1-4alkyl, cyano, hydroxy, C1-4cycloalkoxy, C1-4alkylthio, haloC1-4alkoxy, nitro, Q, (CH2)pQ, NR2R3, -(CH2)pNR2R3 and -O(CH2)pNR2R3; wherein J is substituted at positions meta to each other by NH and Y; and Z is phenyl or pyridyl optionally substituted with one or two substituents independently selected from halogen, haloC1-4alkyl, C1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, nitro and amino; Q is phenyl, a five-membered heterocyclic ring containing one, two, three or four heteroatoms chosen from O, N and S, at most one heteroatom being O or S, or a six-membered heterocyclic ring containing one, two or three nitrogen atoms, optionally substituted by C1-4alkyl; each R2 and R3 is chosen from H and C1-4alkyl, or R2 and R3, together with the nitrogen atom to which they are attached, may form a six-membered ring optionally containing an oxygen atom or a further nitrogen atom, which ring is optionally substituted by C1-4alkyl or Q; p is 1, 2 or 3; or a pharmaceutically acceptable salt thereof; pharmaceutical compositions comprising it; its use in methods of therapy; use of it for manufacturing medicaments; and methods of using it to treat diseases requiring administration of a VR1 antagonist such as pain, cough, GERD and depression.

QUINAZOLINE DERIVATIVES AS ANGIOGENESIS INHIBITORS

The invention relates to the use of compounds of the formula I: wherein ring C is an 8, 9, 10, 12 or 13-membered bicyclic or tricyclic moiety which optionally may contain 1-3 heteroatoms selected independently from O, N and S; Z is -O-, -NH-, -S-, -CH2- or a direct bond; n is 0-5; m is 0-3; R represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, -NRR (wherein R and R, which may be the same or different, each represents hydrogen or C1-3alkyl), or RX- (wherein X and R are as defined herein; R represents hydrogen, oxo, halogeno, hydroxy, C1-4alkoxy, C1-4alkyl, C1-4alkoxymethyl, C1-4alkanoyl, C1-4haloalkyl, cyano, amino, C2-5alkenyl, C2-5alkynyl, C1-3alkanoyloxy, nitro, C1-4alkanoylamino, C1-4alkoxycarbonyl, C1-4alkylsulphanyl, C1-4alkylsulphinyl, C1-4alkylsulphonyl, carbamoyl, N-C1-4alkylcarbamoyl, N,N-di(C1-4alkyl)carbamoyl, aminosulphonyl, N-C1-4alkylaminosulphonyl, N,N-di(C1-4alkyl)aminosulphonyl, N-(C1-4alkylsulphonyl)amino, N-(C1-4alkylsulphonyl)-N-(C1-4alkyl)amino, N,N-di(C1-4alkylsulphonyl)amino, a C3-7alkylene chain joined to two ring C carbon atoms, C1-4alkanoylaminoC1-4alkyl, carboxy or a group RX (wherein X and R are as defined herein); and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.