38092-89-6

Basic information

• Product Name: 8-Chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
• Synonyms: 8-chloro-11-(1-methyl-4-piperidylidenel-5,11)-dihydro-5H-benzo5,6-cyclohepta;6,11ihydro-5H-Benzo-5,6Cyclohepta-L,2-BPyridine,Loratadine;Methyl loratadine;8-Chloro-6,11-dihydro-11(N-Methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;Loratadine Related CoMpound B;Loratadine Related Compound B (15 mg) (8-Chloro-6,11-dihydro-11-(N-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine);8-Chloro-6,11-dihydro-11-(1-Methyl-4-piperidinylid;8-Chloro-6,11-dihydro-11-(1-Methyl-4-piperidinylidene)-
• CAS NO: 38092-89-6
• Molecular Formula: C₂₀H₂₁ClN₂
• Molecular Weight: 324.85
• EINECS: 641-012-1
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;(intermediate of loratadine);Chemical Amines
• Mol File: 38092-89-6.mol

Chemical Properties

• Melting Point: 106-109°C
• Boiling Point: 474.3 °C at 760 mmHg
• Flash Point: 240.7 °C
• Appearance: Red oil
• Density: 1.205 g/cm³
• Vapor Pressure: 3.64E-09mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: -20?C Freezer
• PKA: 8.67±0.20(Predicted)
• CAS DataBase Reference: 8-Chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine(38092-89-6)
• EPA Substance Registry System: 8-Chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine(38092-89-6)

Safety Data

• Hazardous Substances Data: 38092-89-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H21ClN2/c1-23-11-8-14(9-12-23)19-18-7-6-17(21)13-16(18)5-4-15-3-2-10-22-20(15)19/h2-3,6-7,10,13H,4-5,8-9,11-12H2,1H3

Upstream product

• 130642-50-1 {3-[2-(3-Chloro-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone 
• 5570-77-4 4-chloro-1-methylpiperidine 
• 100643-71-8 descarboethoxyloratadine 
• 74-88-4 methyl iodide 
• 31251-41-9 8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one 
• 38089-93-9 8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol 
• 620-20-2 1-Chloro-3-chloromethyl-benzene 
• 63463-36-5 (1-methyl-4-piperidyl)magnesium chloride 
• 107285-30-3 3-<2-(3-chlorophenyl)ethyl>-N-(1,1-dimethylethyl)-2-pyridinecarboxamide 
• 31255-57-9 3-[2-(3-chlorophenyl)ethyl]-2-pyridine-carbonitrile 
• 32998-95-1 N-tert-butyl-3-methylpyridine-2-carboxamide 
• 20970-75-6 2-cyano-3-methylpyridine 
• 119770-60-4 1-(METHYL-4-PIPERIDINYL)[3-(2-(3-CHLORO-PHENYL)ETHYL)-2-PYRIDINYL]METHANONE HYDROCHLORIDE 
• 75-75-2 methanesulfonic acid 

Downstream Products

• 1373612-35-1 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-(2-methoxyphenyl)-1-piperidinecarbothioamide 
• 1373612-32-8 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-cyclohexyl-1-piperidinecarbothioamide 
• 1373612-33-9 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-phenyl-1-piperidinecarbothioamide 
• 1373612-34-0 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-(2-methylphenyl)-1-piperidinecarbothioamide 
• 3964-81-6 azatadine 
• 79794-75-5 loratadine 
• 117810-92-1 (4-(8-chloro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(6H)-ylidene)piperidin-1-yl)(phenyl)methanone 
• 117796-52-8 N-acetyl desloratadine 
• 117810-61-4 N-formyldesloratadine 
• 100643-71-8 descarboethoxyloratadine 

Relevant articles and documents

Preparation method of loratadine

The invention provides a preparation method of loratadine. The method comprises the following steps: taking 2-cyano-3-methylpyridine as a raw material, and carrying out Ritter reaction, m-chlorobenzylchloride condensation, POCl3 deprotection group, Grignard reaction, cyclization and ethyl chloroformate substitution to obtain 4(8-chlorine-5, 6-dihydro-11H-benzo-[5, 6]cycloheptano[1, 2-b]pyridine-11-subunit)-1-piperidine carboxylic acid ethyl ester. According to the invention, a post-treatment process is innovated, and a new cyclization system is adopted to catalyze the reaction, so that the use of high-cost and high-toxicity strong acid is avoided, and a milder and more economical synthesis method is provided for industrial production.

Loratadine and analogues: Discovery and preliminary structure-activity relationship of inhibitors of the amino acid transporter B0AT2

B0AT2, encoded by the SLC6A15 gene, is a transporter for neutral amino acids that has recently been implicated in mood and metabolic disorders. It is predominantly expressed in the brain, but little is otherwise known about its function. To identify inhibitors for this transporter, we screened a library of 3133 different bioactive compounds. Loratadine, a clinically used histamine H1 receptor antagonist, was identified as a selective inhibitor of B0AT2 with an IC50 of 4 μM while being less active or inactive against several other members of the SLC6 family. Reversible inhibition of B0AT2 was confirmed by electrophysiology. A series of loratadine analogues were synthesized to gain insight into the structure-activity relationships. Our studies provide the first chemical tool for B0AT2.

Design and synthesis of thiourea derivatives containing a benzo[5,6]cyclohepta[1,2-b]pyridine moiety as potential antitumor and anti-inflammatory agents

Thiourea derivatives (6a-e) were developed and screened for antitumor and anti-inflammatory activity. Most of the compounds exhibited growth inhibitory effects comparable to 5-fluorouracil in vitro against mammary (MCF-7 and MDA-MB 231) as well as colon (HT-29) carcinoma cells. They also showed stronger anti-inflammatory activity than ibuprofen in vivo in the xylene-induced ear swelling assay in mice.

A PROCESS FOR THE MANUFACTURING OF LORATADINE AND ITS INTERMEDIATES

The process comprises (i) subjecting substituted benzyl halide to cyanation in a biphasic system using water immiscible solvents by any known methods, (ii) condensing in situ the phenyl acetonitrile thus obtained with nicotinic ester in presence of alkali metal alkoxide and water immiscible organic solvent to produce ketonitrile, (iii) hydrolyzing followed by decarboxylating the said ketonitrile in situ to respective ketone in acid environment below 60° C, (iv) subjecting the ketone so obtained to reduction followed by N-oxidation, cyanation, and hydrolysis by any known methods to produce picolinic acid, (v) cyclising the said picolinic acid to tricyclic ketone by conventional methods, (vi) treating the said tricyclic ketone with organometallic compound containing Mg to produce carbinol, (viii) purifying the said carbinol with purifying agent selected from polar water miscible organic solvent followed by dehydrating with neat sulphuric acid at the temperature below 50° C, to get N-methyl product (olefin), and subjecting the said olefin to N-carbethoxylation to produce loratadine. Loratadine can also be prepared by treating cayano compound with organometallic compound containing Mg to produce a ketone by the methods known in the art followed by cyclising in presence of a mixture of sulfuric acid and a source of boric acid to get N-methyl product and converting to loratadine by N-carbethoxylation.

PROCESS FOR THE PREPARATION OF LORATADINE

A process for the production of loratadine chemically known as 8-chloro-11-(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cycloheptal[1,2-B]pyridene has been described. The process comprises reacting a tri-cyclic aromatic ketone with an organometallic compound containing Mg in presence of organic solvent then hydrolyzing and isolating loratadine by conventional methods wherein the reaction between cyclic ketone and the said organometallic compound is effected at a glacial temperature.

Tricyclic carbamate compounds useful for inhibition of G-protein function and for treatment of proliferative diseases

A method of inhibiting Ras function and therefore inhibiting cellular growth is disclosed. The method comprises the administration of a compound of Formula 1.0 Also disclosed are novel compounds of the formulas: Also disclosed are processes for making 3-substituted compounds of the Formulas 1.1, 1.2 and 1.3. Further disclosed are novel compounds which are intermediates in the processes for making the 3-substituted compounds of Formulas 1.1, 1.2, and 1.3.

Tricyclic amide and urea compounds useful for inhibition of g-protein function and for treatment of proliferative diseases

A method of inhibiting Ras function and therefore inhibiting the abnormal growth of cells is disclosed. The method comprises the administration of a compound of Formula 1.0: STR1 to a biological system. In particular, the method inhibits the abnormal growth of cells in a mammal such as a human being. Novel compounds of formulas 5.0, 5.1 and 5.2, wherein R is --C(R20)(R21)(R46), and 5.3, 5.3A and 5.3B, wherein R is --N(R25)(R48), are disclosed. Also disclosed are processes for making 3-substituted compounds of Formulas 5.0, 5.1, 5.2 and 5.3. Further disclosed are novel compounds which are intermediates in the process for making 3-substituted compounds of Formulas 5.0, 5.1, 5.2 and 5.3.

Tricyclic carbamate compounds useful for inhibition of G-protein function and for treatment of proliferative diseases

A method of inhibiting Ras function and therefore inhibiting cellular growth is disclosed. The method comprises the administration of a compound of Formula 1.0 STR1 Also disclosed are novel compounds of the formulas: STR2 Also disclosed are processes for making 3-substituted compounds of the Formulas 1.1, 1.2 and 1.3. Further disclosed are novel compounds which are intermediates in the processes for making the 3-substituted compounds of Formulas 1.1, 1.2, and 1.3.

Tricyclic amide and urea compounds useful for inhibition of G-protein function and for treatment of proliferative diseases

Novel compounds of Formula (7.0a), (7.0b) or (7.0c): STR1 are disclosed. Also disclosed is a method of inhibiting Ras function and therefore inhibiting the abnormal growth of cells. The method comprises administering a compound of the formula (7.0a), (7.0b) or (7.0c) to a biological system. In particular, the method inhibits the abnormal growth of cells in a mammal such as a human being.

Tricyclic sulfonamide compounds useful for inhibition of G-protein function and for treatment of proliferative diseases

A method of inhibiting Ras function and therefore inhibiting cellular growth is disclosed. The method comprises the administration of a compound containing a tricyclic ring system to a biological system. In particular, the method inhibits cellular growth in a mammal such as a human being. Novel compounds of the formula: STR1 are disclosed. Also disclosed are processes for making 3-substituted compounds of Formula 4.0. Further disclosed are novel compounds which are intermediates in the processes for making the 3-substituted compounds of Formula 4.0.