164082-77-3

Usage

Uses

Used in Agriculture:
Metolachlor is used as a herbicide for the control of annual grasses and small-seeded broadleaf weeds in various crops such as soybeans, corn, and peanuts. It is effective in inhibiting the germination of target weed seeds and disrupting the early growth stages of the plant, ultimately leading to its death. This helps to protect the crops and increase their yield.
Used in Regulatory Scrutiny:
Metolachlor has been the subject of controversy and regulatory scrutiny due to its potential impact on human health and the environment. As a restricted use pesticide, it is important to ensure that it is used responsibly and in accordance with regulations to minimize any potential risks.
Used in Environmental Protection:
Due to its potential environmental and human health risks, metolachlor is used with caution and under strict guidelines to protect the environment. Efforts are made to minimize its impact on non-target organisms and ecosystems, and to promote sustainable agricultural practices.

Upstream product

• 75-65-0 tert-butyl alcohol 
• 55289-06-0 3-methoxy-2-methylbenzoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 19500-02-8 2-methyl-3-methoxyaniline 

Downstream Products

• 172733-40-3 1-[2-(tert-butoxycarbonylamino)-6-methoxyphenyl]-2-pentanone 
• 164083-26-5 1-(2-(tert-butoxycarbonylamino)-6-methoxyphenyl)-2-propanone 
• 1045866-39-4 3-methoxy-2-methylaniline trifluoroacetate 
• 19500-02-8 2-methyl-3-methoxyaniline 
• 164083-57-2 1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-methyl-1H-indole-3-acetamide 
• 1027853-40-2 [1-(3-Chloro-benzyl)-2-ethyl-4-methoxy-1H-indol-3-yl]-oxo-acetyl chloride 
• 164082-83-1 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide 
• 164082-86-4 1-[(3-chlorophenyl)methyl]-2-ethyl-4-methoxy-1H-indole 
• 164082-80-8 1-benzyl-2-ethyl-4-methoxy-1H-indole 
• 164082-79-5 2-Ethyl-4-methoxy-1H-indole 
• 164083-55-0 1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester 
• 164083-56-1 1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-methyl-1H-indole-3-acetic acid hydrazide 
• 185063-93-8 [1-(3-Chloro-benzyl)-4-methoxy-2-methyl-1H-indol-3-yl]-acetic acid ethyl ester 
• 185063-74-5 [1-(3-Chloro-benzyl)-4-methoxy-2-methyl-1H-indol-3-yl]-acetic acid hydrazide 

Relevant academic research and scientific papers

Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350

SAR analysis performed with a limited set of cyclopentane-containing macrocycles led to the identification of N-[17-[2-(4-isopropylthiazole-2-yl)-7-methoxy-8-methylquinolin-4-yloxy]- 13-methyl-2,14-dioxo-3,13-diazatricyclo [13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamid e (TMC435350, 32c) as a potent inhibitor of HCV NS3/4A protease (Ki = 0.36 nM) and viral replication (replicon EC50 = 7.8 nM). TMC435350 also displayed low in vitro clearance and high permeability, which were confirmed by in vivo pharmacokinetic studies. TMC435350 is currently being evaluated in the clinics.

Discovery of novel potent and selective dipeptide hepatitis C virus NS3/4A serine protease inhibitors

Starting from the previously reported HCV NS3/4A protease inhibitor BILN 2061 (1), we have used a fast-follower approach to identify a novel series of HCV NS3/4A protease inhibitors in which (i) the P3 amino moiety and its capping group have been truncated, (ii) a sulfonamide is introduced in the P1 cyclopropyl amino acid, (iii) the position 8 of the quinoline is substituted with a methyl or halo group, and (iv) the ring size of the macrocycle has been reduced to 14 atoms. SAR analysis performed with a limited set of compounds led to the identification of N-{17-[8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2,14-dioxo-3,15-diazatricyclo [13.3.0.0 [Bartenschlager, R.; Lohmann, V. J. Gen. Virol. 2000, 81, 1631; Vincent Soriano, Antonio Madejon, Eugenia Vispo, Pablo Labarga, Javier Garcia-Samaniego, Luz Martin-Carbonero, Julie Sheldon, Marcelle Bottecchia, Paula Tuma, Pablo Barreiro Expert Opin. Emerg. Drugs, 2008, 13, 1-19]]octadec-7-ene-4-carbonyl}(1-methylcyclopropyl)(1-methylcyclopropyl)sulfonamide 19l an extremely potent (Ki = 0.20 nM, EC50 = 3.7 nM), selective, and orally bioavailable dipeptide NS3/4A protease inhibitor, which has features attractive for further preclinical development.

HCV INHIBITING MACROCYCLIC PHOSPHONATES AND AMIDOPHOSPHATES

Inhibitors of HCV replication of Formula (I) the /V-oxides, salts, and stcreochcmically isomeric forms thereof; pharmaceutical compositions containing compounds (1) and processes for preparin compounds (I). The side chain R2 is an amidophosphate or a phosphonate group and X, R1, R3, E and n are as defined in the application.

POLYMORPHIC FORMS OF A MACROCYCLIC INHIBITOR OF HCV

Provided are crystalline forms of the compound of formula (I), which is a macrocyclic inhibitor of HCV, processes for the preparation thereof, and pharmaceutical compositions comprising these crystalline forms.

AZAINDOLE COMPOUNDS AND USE THEREOF AS PHOSPHOLIPASE-A2 INHIBITORS

Indole and indole-related compounds, compositions and methods are disclosed. The compounds of the invention are useful as phospholipase inhibitors. The compounds and compositions of the invention are useful for treatment of phospholipase-related conditions, such as insulin-related, weight-related and/or cholesterol-related conditions in an animal subject.

INDOLE COMPOUNDS HAVING C4-AMIDE SUBSTITUENTS AND USE THEREOF AS PHOSPHOLIPASE-A2 INHIBITORS

Indole and indole-related compounds, compositions and methods are disclosed. The compounds of the invention are useful as phospholipase inhibitors. The compounds and compositions of the invention are useful for treatment of phospholipase-related conditions, such as insulin-related, weight-related and/or cholesterol-related conditions in an animal subject.

PHOSPHOLIPASE INHIBITORS, INCLUDING MULTI-VALENT PHOSPHOLIPASE INHIBITORS, AND USE THEREOF, INCLUDING AS LUMEN-LOCALIZED PHOSPHOLIPASE INHIBITORS

The present invention provides methods and compositions for the treatment of phospholipase-related conditions. In particular, the invention provides a method of treating insulin-related, weight-related conditions and/or cholesterol-related conditions in an animal subject. The method generally involves the administration of a non-absorbed and/or effluxed phospholipase A2 inhibitor that is localized in a gastrointestinal lumen.

INDOLE COMPOUNDS HAVING C4-ACIDIC SUBSTITUENTS AND USE THEREOF AS PHOSPHOLIPASE-A2 INHIBITORS

Indole and indole-related compounds, compositions and methods are disclosed. The compounds of the invention are useful as phospholipase inhibitors. The compounds and compositions of the invention are useful for treatment of phospholipase-related conditions, such as insulin-related, weight-related and/or cholesterol-related conditions in an animal subject.

Multivalent indole compounds and use thereof as phospholipase-A2 inhibitors

Indole and indole-related compounds, compositions and methods are disclosed. The compounds of the invention are useful as phospholipase inhibitors. The compounds and compositions of the invention are useful for treatment of phospholipase-related conditions, such as insulin-related, weight-related and/or cholesterol-related conditions in an animal subject.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl; R4 is aryl or Het; n is 3, 4, 5, or 6; R5 is halo, C1-6alkyl, hydroxy, C1-6alkoxy, phenyl, or Het; R6 is C1-6alkoxy, or dimethylamino; R7 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R8 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents ; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.