139583-91-8

Upstream product

• 66897-25-4 4-methoxy-N-prop-2-enylbenzamide 
• 74-88-4 methyl iodide 
• 31310-08-4 2-methyl-4-methoxybenzoyl chloride 
• 6245-57-4 4-methoxy-2-methylbenzoic acid 

Downstream Products

• 900174-96-1 (E)-4-methoxy-2-methylbenzoyl-(N,N-dimethyl)formamidine 
• 1377582-21-2 4-Methoxy-2-methyl-5-nitro-benzamide 
• 1377582-22-3 5-Amino-4-methoxy-2-methyl-benzamide 
• 1377582-23-4 5-Isothiocyanato-4-methoxy-2-methyl-benzamide 
• 1377582-24-5 4-methoxy-2-methyl-5-thioureido-benzamide 
• 266690-48-6 1-amino-6-methoxy-isoquinoline 
• 132997-77-4 1-chloro-6-methoxyisoquinoline 
• 26829-43-6 6-methoxy-2H-isoquinolin-1-one 

Relevant academic research and scientific papers

PYRIDYL-THIAZOLYL INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to thiazole I and its therapeutic and prophylactic uses, wherein the variables Rz, Q, J, R1, R3, R5, and R6 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

BISTHIAZOLE INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to bisthiazole I and its therapeutic and prophylactic uses, wherein the variables A, R5, R6, and R7 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

TRICYCLIC INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to tricycle I and its therapeutic and prophylactic uses, wherein the variables C1, C2, Z1, Z2, Q, J, R1, and R3 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

PHENYL-THIAZOLYL INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to phenyl thiazole I and its therapeutic and prophylactic uses, wherein the variables Rz, Q, J, R1, R3, R5, R6, and R7 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

FUSED HETEROARYL INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to thiazole I and its therapeutic and prophylactic uses, wherein the variables A, Q, J, R1, R3, and R5 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

PROCESS FOR THE PREPARATION OF SUBSTITUTED HETEROCYCLES

The present disclosure generally relates to a process for the preparation of hydroxy-substituted heterocycles such as isoquinolines, naphthyridines, pyridopyridazines, and pyridopyrimidines.

2-(ARYLOXY)ACETAMIDE FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS

The present invention relates generally to novel 2-(aryloxy)acetamides of Formula (I) or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, or prodrugs thereof, wherein the variables W, Y, Z, R7, R8, and R9 are as defined herein. These compounds are selective inhibitors of the serine protease coagulation factor VIIa which can be used as medicaments.

PHENYLGLYCINAMIDE DERIVATIVES USEFUL AS ANTICOAGULANTS

The present invention relates generally to phenylglycinamide derivatives that inhibit serine proteases. In particular it is directed to novel phenylglycinamide derivatives, and analogues thereof, which are useful as selective inhibitors of serine protease enzymes of the coagulation cascade; for example thrombin, factor VIIa, factor Xa, factor XIa, factor IXa, and/or plasma kallikrein. In particular, it relates to compounds that are factor VIIa inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same.

Heteroatom-Directed Metalation. Lithiation of N-Propenylbenzamides and N-Propenyl-o-toluamides. Novel Routes to Ortho-Substituted Primary Benzamide Derivatives and N-Unsubstituted Isoquinolin-1(2H)-ones

Reaction of N-propenylbenzamides 4 and 9, obtained by LDA-induced isomerization of the corresponding N-allylbenzamides, 1, 8, and 14, with 2 equiv of sec-butyllithium or tert-butyllithium at low temperature regiospecifically generates the highly reactive N,ortho-dilithiated species (e.g., 5 and 17).These dilithio species react avidly with a wide spectrum of electophilic reagents, including alky halides, giving adducts which on hydrolysis with warm 50percent aqueous acetic acid are converted into ortho-substituted primary benzamides in excellent yields.Ortho-lithiation of N-propenylbenzamides is thus formally equivalent to ortho-lithiation of primary benzamides themselves.The utility of this important, previously unknown, synthetic operation is enhanced by the well-known facility with which the primary amide moiety can be transformed into other useful functional groups, as exemplified by the synthesis of 2-methoxy-6-methylbenzoic acid (12) and 2-methoxy-6-methylbenzonitrile (13) from N-propenyl-2-methoxybenzamide (9).N-Propenyl-o-toluamide (7) undergoes regiospecific dilithiation on nitrogen and on the methyl group under conditions analogous to those used for the N-propenylbenzamides.These dilithio species react with DMF or "Weinreb type" amides to give condensation products which cyclize to N-propenylisoquinolin-1(2H)-ones under mildly acidic conditions.Removal of the N-propenyl moiety under more strongly acidic conditions provides N-unsubstituted isoquinolin-1(2H)-ones with high overall efficiency.This process is exemplified by the synthesis of isoquinolin-1(2H)-one (23) and its 3-n-butyl congener 26 from N-propenyl-2-methylbenzamide (7).