249889-68-7

Basic information

• Product Name: 8-CHLORO-2-METHOXY-1,5-NAPHTHYRIDINE
• Synonyms: 8-CHLORO-2-METHOXY-1,5-NAPHTHYRIDINE;4-Chloro-6-Methoxy-1,5-naphthyridine;8-Chloro-2-(methyloxy)-1,5-naphthyridine
• CAS NO: 249889-68-7
• Molecular Formula: C₉H₇ClN₂O
• Molecular Weight: 194.61768
• Product Categories: Heterocycle-Pyridine series
• Mol File: 249889-68-7.mol

Chemical Properties

• Boiling Point: 287.4±35.0 °C(Predicted)
• Appearance: /
• Density: 1.333±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.39±0.10(Predicted)
• CAS DataBase Reference: 8-CHLORO-2-METHOXY-1,5-NAPHTHYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-CHLORO-2-METHOXY-1,5-NAPHTHYRIDINE(249889-68-7)
• EPA Substance Registry System: 8-CHLORO-2-METHOXY-1,5-NAPHTHYRIDINE(249889-68-7)

Safety Data

• Hazardous Substances Data: 249889-68-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-CHLORO-2-METHOXY-1,5-NAPHTHYRIDINE is used as a building block in the synthesis of various pharmaceutical products due to its potential biological activities. Its antimicrobial and antifungal properties make it a promising candidate for the development of new drugs to combat infections and diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 8-CHLORO-2-METHOXY-1,5-NAPHTHYRIDINE is utilized as a precursor in the synthesis of agrochemical products. Its antimicrobial and antifungal properties can be harnessed for the development of new pesticides and fungicides to protect crops and enhance agricultural productivity.
Used in Research Applications:
8-CHLORO-2-METHOXY-1,5-NAPHTHYRIDINE is also used in research settings to explore its potential applications and properties further. Its unique structure and biological activities make it an interesting subject for scientific investigations, which could lead to the discovery of new therapeutic agents and agrochemical products.

Upstream product

• 23443-25-6 6-methoxy-1,5-naphthyridin-4-ol 
• 53241-85-3 6-methoxy-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid 
• 23443-25-6 6-methoxy-1,5-naphthyridin-4(1H)-one 
• 6628-77-9 6-methoxy-pyridin-3-ylamine 
• 25063-69-8 5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 

Downstream Products

• 952059-81-3 tert-butyl 2-[2-methoxy-4-(6-methoxy-1,5-naphthyridin-4-yloxy)phenyl]acetate 
• 952059-87-9 methyl 2-[3-methoxy-5-(6-methoxy-1,5-naphthyridin-4-yloxy)pyridin-2-yl]acetate 
• 952059-80-2 2-[2-methoxy-4-(6-methoxy-1,5-naphthyridin-4-yloxy)phenyl]acetic acid 
• 1092565-26-8 N-(2,4-difluorophenyl)-5-[8-(4-methyl-1-piperazinyl)-1,5-naphthyridin-2-yl]-3-pyridinesulfonamide 
• 1092565-36-0 N-[5-(8-{4-[(dimethylamino)methyl]phenyl}-1,5-naphthyridin-2-yl)-3-pyridinyl]benzenesulfonamide 
• 1092565-41-7 N-{5-[8-(4-hydroxy-1-piperidinyl)-1,5-naphthyridin-2-yl]-3-pyridinyl}benzenesulfonamide 
• 1092565-25-7 N-(2,4-difluorophenyl)-5-[8-(3-thienyl)-1,5-naphthyridin-2-yl]-3-pyridinesulfonamide 
• 1092565-23-5 N-(2,4-difluorophenyl)-5-[8-(2-furanyl)-1,5-naphthyridin-2-yl]-3-pyridinesulfonamide 
• 1092565-40-6 N-{5-[8-(4-morpholinyl)-1,5-naphthyridin-2-yl]-3-pyridinyl}benzenesulfonamide 
• 1092565-24-6 5-(8-chloro-1,5-naphthyridin-2-yl)-N-(2,4-difluorophenyl)-3-pyridinesulfonamide 
• 1092565-19-9 5-[8-(3-cyanophenyl)-1,5-naphthyridin-2-yl]-3-pyridinesulfonamide 
• 1092565-37-1 N-[5-(8-chloro-1,5-naphthyridin-2-yl)-3-pyridinyl]benzenesulfonamide 

Relevant articles and documents

Aurora Kinase Modulators and Method of Use

The present invention relates to chemical compounds having a general formula I wherein A1-8, D′, L1, L2, R1, R6-8 and n are defined herein, and synthetic intermediates, which are capable of modulating various protein kinase receptor enzymes and, thereby, influencing various disease states and conditions related to the activities of such kinases. For example, the compounds are capable of modulating Aurora kinase thereby influencing the process of cell cycle and cell proliferation to treat cancer and cancer-related diseases. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of Aurora kinase.

AURORA KINASE MODULATORS AND METHOD OF USE

The present invention relates to chemical compounds having a general formula I {INSERT STRUCTURE HERE} wherein A1-8, D,, L1, L2, R1, R6-8 and n are defined herein, and synthetic intermediates, which are capable of modulating various protein kinase receptor enzymes and, thereby, influencing various disease states and conditions related to the activities of such kinases. For example, the compounds are capable of modulating Aurora kinase thereby influencing the process of cell cycle and cell proliferation to treat cancer and cancer-related diseases. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of Aurora kinase.

NAPHTHYRIDINE DERIVATIVES

The invention concerns naphthyridine derivatives of Formula (Ia) or (Ib) or a pharmaceutically-acceptable salt thereof, wherein each of X1, p, R1, G1, G2, q, R2, R3, R4, R5, Ring A, r and R6 has any of the meanings defined hereinbefore in the description; pharmaceutical compositions containing them and their use in the treatment of cell proliferative disorders or disease states associated with angiogenesis and/or vascular permeability.

COMPOUND HAVING TGF-BETA INHIBITORY ACTIVITY AND PHARMACEUTICAL COMPOSITION CONTAINING SAME

The present invention provides compounds of formula (I) or compounds of formula (II) and pharmaceutically acceptable salts or solvates thereof. An objective of the present invention is to provide compounds having TGF2 inhibitory activity.

AMINOPIPERIDINE DERIVATIVES AS ANTIBACTERIALS

From EXEMP_CLAIMS : 1. A compound of formula (I) or a pharmaceutically acceptable N-oxide, salt or ester thereof: wherein: either Z1, Z2, Z3, Z4 and Z5 are CR1a; or one of Z1, Z2, Z3, Z4 and Z5 is N, and the remainder are CR1a; R1 and R1a are independently hydrogen; hydroxy; (C1-6)alkoxy optionally substituted by (C1-6)alkoxy, amino, piperidyl, guanidino or amidino optionally N-substituted by one or two (C1-6)alkyl, acyl or (C1-6)alkylsulphonyl groups, CONH2, hydroxy, thiol, (C1-6)alkylthio, heterocyclylthio, heterocyclyloxy, arylthio, aryloxy, acylthio, acyloxy or (C1-6)alkylsulphonyloxy; (C1-6)alkoxy-substituted (C1-6)alkyl; halogen; (C1-6)alkyl; (C1-6)alkylthio; nitro; azido; acyl; acyloxy; (C1-6)alkylsulphonyl; (C1-6)alkylsulphoxide; arylsulphonyl; arylsulphoxide or an amino, piperidyl, guanidino or amidino group optionally N-substituted by one or two (C1-6)alkyl, acyl or (C1-6)alkylsulphonyl groups; and additionally when Z5 is CR1a, R1a may be (C1-4)alkyl-CO2H or (C1-4)alkyl-CONH2 in which the (C1-4) alkyl is substituted by R12; (C1-4)alkyl substituted by cyano, amino or guanidino; aminocarbonyl optionally substituted by hydroxy, (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylsulphonyl, trifluoromethylsulphonyl, (C2-6)alkenylsulphonyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl, (C2-6)alkenylcarbonyl, or CH(R13)CO2H or CH(R13)CONH2 optionally further substituted by (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl or (C2-6)alkenyl; hydroxy(C1-6)alkyl; carboxy; cyano or (C1-6)alkoxycarbonyl; wherein R13 is a natural α-amino acid side chain or its enantiomer; provided that when Z1, Z2, Z3, Z4 and Z5 are CR1a, then R1 is not hydrogen; R2 is hydrogen, or (C1-4)alkyl or (C2-4)alkenyl optionally substituted with 1 to 3 groups selected from: amino optionally substituted by one or two (C1-4)alkyl groups; carboxy; (C1-4)alkoxycarbonyl; (C1-4)alkylcarbonyl; (C2-4)alkenyloxycarbonyl; (C2-4)alkenylcarbonyl; aminocarbonyl wherein the amino group is optionally substituted by hydroxy, (C1-4)alkyl, hydroxy(C1-4)alkyl, aminocarbonyl(C1-4)alkyl, (C2-4)alkenyl, (C1-4)alkylsulphonyl, trifluoromethylsulphonyl, (C2-4)alkenylsulphonyl, (C1-4)alkoxycarbonyl, (C1-4)alkylcarbonyl, (C2-4)alkenyloxycarbonyl or (C2-4)alkenylcarbonyl; cyano; tetrazolyl; 2-oxo-oxazolidinyl optionally substituted by R10; 3-hydroxy-3-cyclobutene-1,2-dione-4-yl; 2,4-thiazolidinedione-5-yl; tetrazol-5-ylaminocarbonyl; 1,2,4-triazol-5-yl optionally substituted by R10; 5-oxo-1,2,4-oxadiazol-3-yl; thiol; halogen; (C1-4)alkylthio; trifluoromethyl; azido; hydroxy optionally substituted by (C 1-4)alkyl, (C2-4)alkenyl, (C1-4)alkoxycarbonyl, (C1-4)alkylcarbonyl, (C2-4)alkenyloxycarbonyl, (C2-4)alkenylcarbonyl; oxo; (C1-4)alkylsulphonyl; (C2-4)alkenylsulphonyl; or (C1-4)aminosulphonyl wherein the amino group is optionally substituted by (C1-4)alkyl or (C2-4)alkenyl; R3 is hydrogen; or R3 is in the 2-, 3- or 4-position and is: carboxy; (C1-6)alkoxycarbonyl; aminocarbonyl wherein the amino group is optionally substituted by hydroxy, (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylsulphonyl, trifluoromethylsulphonyl, (C1-6)alkenylsulphonyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl or (C2-6)alkenylcarbonyl and optionally further substituted by (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl or (C2-6)alkenyl; cyano; tetrazolyl; 2-oxo-oxazolidinyl optionally substituted by R10; 3-hydroxy-3-cyclobutene-1,2-dione-4-yl; 2,4-thiazolidinedione-5-yl; tetrazol-5-ylaminocarbonyl; 1,2,4-triazol-5-yl optionally substituted by R10; or 5-oxo-1,2,4-oxadiazol-3-yl; or (C 1-4)alkyl optionally substituted, or ethenyl substituted, with any of the substituents listed above for R3 and up to 3 groups R12 independently selected from: thiol; halogen; (C1-6)alkylthio; trifluoromethyl; azido; (C1-6)alkoxycarbonyl; (C1-6)alkylcarbonyl; (C2-6)alkenyloxycarbonyl; (C2-6)alkenylcarbonyl; hydroxy optionally substituted by (C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl, (C2-6)alkenylcarbonyl or aminocarbonyl wherein the amino group is optionally substituted by (C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylcarbonyl or (C2-6)alkenylcarbonyl; amino optionally mono- or disubstituted by (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl, (C2-6)alkenylcarbonyl, (C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylsulphonyl, (C2-6)alkenylsulphonyl or aminocarbonyl wherein the amino group is optionally substituted by (C1-6)alkyl or (C2-6)alkenyl; aminocarbonyl wherein the amino group is optionally substituted by (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl or (C2-6)alkenylcarbonyl and optionally further substituted by (C 1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl or (C2-6)alkenyl; oxo; (C1-6)alkylsulphonyl; (C2-6)alkenylsulphonyl; or (C1-6)aminosulphonyl wherein the amino group is optionally substituted by (C1-6)alkyl or (C2-6)alkenyl; in addition when R3 is disubstituted with a hydroxy or amino containing substituent and carboxy containing substituent these may together form a cyclic ester or amide linkage, respectively; or when R3 is in the 3- or 4-position it may with R2 or R4 form a C3-5 alkylene group optionally substituted by a group R5 selected from: (C1-12)alkyl; hydroxy(C1-12)alkyl; (C1-12)alkoxy(C1-12)alkyl; (C1-12)alkanoyloxy(C1-12)alkyl; (C3-6)cycloalkyl; hydroxy(C3-6)cycloalkyl; (C1-12)alkoxy(C3-6)cycloalkyl; (C1-12)alkanoyloxy(C3-6)cycloalkyl; (C3-6)cycloalkyl(C1-12)alkyl; hydroxy-, (C1-12)alkoxy- or (C1-12)alkanoyloxy-(C3-6)cycloalkyl(C1-12)alkyl; cyano; cyano(C1-12)alkyl; (C2-12)alkenyl; (C2-12)alkynyl; tetrahydrofuryl; mono- or di-(C1-12)alkylamino(C1-12)alkyl; acylamino(C1-12)alkyl; (C1-12)alkyl- or acyl-aminocarbonyl(C1-12)alkyl; mono- or di-(C1-12)alkylamino(hydroxy) (C1-12)alkyl; optionally substituted phenyl(C1-12)alkyl, phenoxy(C1-12)alkyl or phenyl(hydroxy)(C1-12)alkyl; optionally substituted diphenyl(C1-12)alkyl; optionally substituted phenyl(C2-12)alkenyl; optionally substituted benzoyl or benzoyl(C1-12)alkyl; optionally substituted heteroaryl or heteroaryl(C1-12)alkyl; and optionally substituted heteroaroyl or heteroaroyl(C1-12)alkyl; R4 forms a group with R3 as above defined, or is a group -CH2-R5 where R5 is as defined above: n is 0, 1 or 2; A is NR11 or CR6R7 and B is NR11, O, SO2 or CR8R9 and wherein: each of R6, R7, R8 and R9 is independently selected from: hydrogen; (C1-6)alkylthio; halo; trifluoromethyl; azido; (C1-6)alkyl; (C2-6)alkenyl; (C1-6)alkoxycarbonyl; (C1-6)alkylcarbonyl; (C2-6)alkenyloxycarbonyl; (C2-6)alkenylcarbonyl; hydroxy, amino or aminocarbonyl optionally substituted as for corresponding substituents R12 in R3; (C1-6)alkylsulphonyl; (C2-6)alkenylsulphonyl; or aminosulphonyl wherein the amino group is optionally substituted by (C1-6)alkyl or (C1-6)alkenyl; or R6 and R8 together represent a bond and R7 and R9 are as above defined; or R6 and R7 or R8 and R9 together represent oxo; provided that: when A is NR11, B is not NR11, O or SO2; when A is CO, B is not CO, O or SO2; when n is 0 and A is NR11, CR8R9 can only be CO; when A is CR6R7 and B is SO2, n is 0; when n is 0, B is not NR11 or O; and when A-B is CR7=CR9, n is 1 or 2; R10 is selected from (C1-4)alkyl; (C2-4)alkenyl and aryl any of which may be optionally substituted by a group R12 as defined above; carboxy; aminocarbonyl wherein the amino group is optionally substituted by hydroxy, (C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylsulphonyl, trifluoromethylsulphonyl, (C2-6)alkenylsulphonyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl or (C2-6)alkenylcarbonyl and optionally further substituted by (C1-6)alkyl or (C2-6)alkenyl; (C1-6)alkylsulphonyl; trifluoromethylsulphonyl; (C2-6)alkenylsulphonyl; (C1-6)alkoxycarbonyl; (C1-6)alkylcarbonyl; (C2-6)alkenyloxycarbonyl; and (C2-6)alkenylcarbonyl; R11 is hydrogen; trifluoromethyl, (C1-6)alkyl; (C2-6)alkenyl; (C1-6)alkoxycarbonyl; (C1-6)alkylcarbonyl; aminocarbonyl wherein the amino group is optionally substituted by (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl, (C2-6)alkenylcarbonyl, (C1-6)alkyl or (C2-6)alkenyl and optionally further substituted by (C1-6)alkyl or (C2-6)alkenyl; wherein optionally substituted phenyl, benzoyl, heteroaryl and heteroaroyl groups are optionally substituted with up to five groups selected from halogen, mercapto, (C1-6)alkyl, phenyl, (C1-6)alkoxy, hydroxy(C1-6)alkyl, mercapto (C1-6)alkyl, halo(C1-6)alkyl, hydroxy, amino, nitro, carboxy, (C1-6)alkylcarbonyloxy, (C1-6)alkoxycarbonyl, formyl, and (C1-6)alkylcarbonyl groups.

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