444807-46-9

Basic information

• Product Name: METHYL 4-AMINOMETHYLPHENYLACETATE
• Synonyms: METHYL 4-AMINOMETHYLPHENYLACETATE;Methyl 4-aminomethylphenylacetate HCl;Methyl 4-aminomethylphenylacetate hydrochloride;Benzeneacetic acid, 4-(aMinoMethyl)-, Methyl ester;methyl 2-(4-(aminomethyl)phenyl)acetate
• CAS NO: 444807-46-9
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Product Categories: pharmacetical
• Mol File: 444807-46-9.mol

Chemical Properties

• Boiling Point: 315.7°Cat760mmHg
• Flash Point: 144.7°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.000316mmHg at 25°C
• CAS DataBase Reference: METHYL 4-AMINOMETHYLPHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-AMINOMETHYLPHENYLACETATE(444807-46-9)
• EPA Substance Registry System: METHYL 4-AMINOMETHYLPHENYLACETATE(444807-46-9)

Safety Data

• Hazardous Substances Data: 444807-46-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H13NO2.ClH/c1-13-10(12)6-8-2-4-9(7-11)5-3-8;/h2-5H,6-7,11H2,1H3;1H

Upstream product

• 67-56-1 methanol 
• 1200-05-1 2-(4-(aminomethyl)phenyl)acetic acid 
• 5462-71-5 4-cyanophenylacetic acid 
• 7398-42-7 methyl 2-(4-(bromomethyl)phenyl)acetate 
• 13737-36-5 4-bromophenylacetic acid 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 52798-01-3 methyl 4-cyanobenzeneacetate 

Downstream Products

• 808753-25-5 [4-(ethanesulfonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 110626-68-1 2-(4-(methanesulfonoamidomethyl)phenyl)acetic acid 
• 191871-32-6 [4-(tert-butoxycarbonylamino-methyl)-phenyl]-acetic acid methyl ester 
• 808753-33-5 [4-(thiophene-2-sulfonylamino-methyl)-phenyl]-acetic acid methyl ester 

Relevant articles and documents

Discovery of carboxyl-containing biaryl ureas as potent RORγt inverse agonists

GSK805 (1) is a potent RORγt inverse agonist, but a drawback of 1 is its low solubility, leading to a limited absorption in high doses. We have explored detailed structure-activity relationship on the amide linker, biaryl and arylsulfonyl moieties of 1 trying to improve solubility while maintaining RORγt activity. As a result, a novel series of carboxyl-containing biaryl urea derivatives was discovered as potent RORγt inverse agonists with improved drug-like properties. Compound 3i showed potent RORγt inhibitory activity and subtype selectivity with an IC50 of 63.8 nM in RORγ FRET assay and 85 nM in cell-based RORγ-GAL4 promotor reporter assay. Reasonable inhibitory activity of 3i was also achieved in mouse Th17 cell differentiation assay (76percent inhibition at 0.3 μM). Moreover, 3i had greatly improved aqueous solubility at pH 7.4 compared to 1, exhibited decent mouse PK profile and demonstrated some in vivo efficacy in an imiquimod-induced psoriasis mice model.

BIARYL UREA DERIVATIVE OR SALT THEREOF, AND MANUFACTURING AND APPLICATION OF SAME

The present invention discloses a biaryl urea RORγt inhibitor, and specifically relates to a biaryl urea derivative, as represented by formula I, with an RORγt inhibiting activity, and a preparation process thereof, and a pharmaceutical composition comprising the compound. Further disclosed is use of the compound for treating an RORγt-related disease.

BIARYL COMPOUND, PREPARATION METHOD AND USE THEREFOR

The present invention belongs to the technical field of chemical pharmaceuticals, and relates to a compound represented by general formula (I) or formula (II) and a preparation method thereof. The compounds are biaryl derivatives with RORγt activation activity. The biaryl derivatives disclosed in this invention can effectively activate the RORγt protein receptor, and thereby promote the differentiation of Th17 cells and increasing the production of IL-17, which can be used as an immune modulator for the treatment of various cancers or viral infection-related diseases.

Glutaminase inhibitors as well as compositions and applications thereof

The invention provides a series of heterocyclic compounds expressed in a formula I. The compound comprises glutaminase inhibition activity, and can be used for treating diseases and symptoms related to dysfunction of glutaminase or raising activity of glutaminase.

A Dual Modulator of Farnesoid X Receptor and Soluble Epoxide Hydrolase to Counter Nonalcoholic Steatohepatitis

Nonalcoholic steatohepatitis arising from Western diet and lifestyle is characterized by accumulation of fat in liver causing inflammation and fibrosis. It evolves as serious health burden with alarming incidence, but there is no satisfying pharmacological therapy to date. Considering the disease's multifactorial nature, modulation of multiple targets might provide superior therapeutic efficacy. In particular, farnesoid X receptor (FXR) activation that revealed antisteatotic and antifibrotic effects in clinical trials combined with inhibition of soluble epoxide hydrolase (sEH) as anti-inflammatory strategy promises synergies. To exploit this dual concept, we developed agents exerting partial FXR agonism and sEH inhibitory activity. Merging known pharmacophores and systematic exploration of the structure-activity relationship on both targets produced dual modulators with low nanomolar potency. Extensive in vitro characterization confirmed high dual efficacy in cellular context combined with low toxicity, and pilot in vivo data revealed favorable pharmacokinetics as well as engagement on both targets in vivo.

Arylacetamide κ opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity

Some κ opioid receptor agonists of the arylacetamide class, for example, ICI 199441 (1), were found to strongly inhibit the activity of cytochrome P450 2D6 (CYP2D6) (1: CYP2D6 IC50 = 26 nM). Certain analogs bearing a substituted sulfonylamino group, for example, 13, were discovered to have significantly reduced CYP2D6 inhibitory activity (13: CYP2D6 IC50 > 10 μM) while displaying high affinity toward the cloned human κ opioid receptor, good κ/δ and κ/μ selectivity, and potent in vitro and in vivo agonist activity.

Nicotinamide derivatives and their mimetics as inhibitors of PDE4 isozymes

Compounds useful as inhibitors of PDE4 in the treatment of diseases regulated by the activation and degranulation of eosinophils, especially asthma, chronic bronchitis, and chronic obstructive pulmonary disease, of the formula: wherein j is 0 or 1, k is 0 or 1, m is 0, 1, or 2;n is 1 or 2; A is is selected from the partial Formulas: where q is 1, 2, or 3, W3 is -O-; -N(R9)-; or -OC(=O)-; R7 is selected from -H; -(C1-C6)alkyl, -(C2-C6)alkenyl, or -(C2-C6)alkynyl substituted by 0 to 3 substituents R10; -(CH2)u-(C3-C7) cycloalkyl where u is 0, 1 or 2, substituted by 0 to 3 R10; and phenyl or benzyl substituted by 0 to 3 R14; R8 is tetrazol-5-yl; 1,2,4-triazol-3-yl; 1,2,4-triazol-3-on-5-yl; 1,2,3-triazol-5-yl; imidazol-2-yl; imidazol-4-yl; imidazolidin-2-on-4-yl; 1,3,4-oxadiazolyl; 1,3,4-oxadiazol-2-on-5-yl; 1,2,4-oxadiazol-3-yl; 1,2,4-oxadiazol-5-on-3-yl; 1,2,4-oxadiazol-5-yl; 1,2,4-oxadiazol-3-on-5-yl; 1,2,5-thiadiazolyl; 1,3,4-thiadiazolyl; morpholinyl; parathiazinyl; oxazolyl; isoxazolyl; thiazolyl; isothiazolyl; pyrrolyl; pyrazolyl; succinimidyl; glutarimidyl; pyrrolidonyl; 2-piperidonyl; 2-pyridonyl; 4-pyridonyl; pyridazin-3-onyl; pyridyl; pyrimidinyl; pyrazinyl; pyridazinyl; indolyl; indolinyl; isoindolinyl; benzo[b]furanyl; 2,3-dihydrobenzofuranyl; 1,3-dihydroisobenzofuranyl; 2H-1-benzopyranyl; 2-H-chromenyl; chromanyl; benzothienyl; 1H-indazolyl; benzimidazolyl; benzoxazolyl; benzisoxazolyl; benzothiazolyl; benzotriazolyl; benzotriazinyl; phthalazinyl; 1,8-naphthyridinyl; quinolinyl; isoquinolinyl; quinazolinyl; quinoxalinyl; pyrazolo[3,4-d]pyrimidinyl; pyrimido[4,5-d]pyrimidinyl; imidazo[1,2-a]pyridinyl; pyridopyridinyl; pteridinyl; or 1H-purinyl; or A is selected from phosphorous and sulfur acid groups; W is ―O―; ―S(=O)t―, where t is 0, 1, or 2; or -N(R3)―; Y is C(R1a)―, or -[N□(O)k] where k is 0 or 1; R4, R5 and R6 are (1)―H; provided that R5 and R6 are not both -H at the same time, ―F; ―Cl; -(C2-C4) alkynyl; -R16; ―OR16; -S(=O)pR16; ―C(=O)R16, -C(=O)OR16; -OC(=O)R16; -CN; -NO2; -C(=O)NR16R17; -OC(=O)NR16R17; ―NR12aC(=O)NR16R17; -NR12aC(=NR12)NR16R17; -NR12aC(=NCN)NR15R16; -NR12aC(=N-NO2)NR15R16; -C(=NR12a)NR15R16; -CH2C(=NR12a)NR16R17; ―OC(=NR12a)NR16R17; ―OC(=N―NO2)NR16R17; -NR16R17; -CH2NR16R17; -NR12aC(=O)R16; -NR12aC(=O)OR16; =NOR16; ―NR12aS(=O)pR17 -S(=O)pNR16R17; and ―CH2C(=NR12a)NR16R17;(2) -(C1-C4) alkyl including dimethyl and -(C1-C4) alkoxy substituted with 0 to 3 substituents ―F or ―Cl; or 0 or 1 substituent (C1-C2) alkoxycarbonyl―, (C1-C2) alkylcarbonyl―, or (C1-C2) alkylcarbonyloxy―; or (3) an aryl or heterocyclic moiety; or (4) R5 and R6 are taken together to form a moiety of partial Formulas (1.3.1) through (1.3.15):B1 and B2 is a moiety comprising a saturated or unsaturated carbon ring system that is 3- to 7-membered monocyclic, or that is 7- to 12-membered, fused or discontinuous, polycyclic; wherein optionally one carbon atom thereof may be replaced by a heteroatom selected from N, O and S; and where N is selected, optionally a second carbon atom thereof may be replaced by a heteroatom selected from N, O, or S; or a pharmaceutically acceptable salt thereof.

The design, synthesis and activity of non-ATP competitive inhibitors of pp60(c-src) tyrosine kinase. Part 2: Hydroxyindole derivatives

As part of continuing effort to identify novel scaffolds that inhibit the pp60(c-src) protein tyrosine kinase, a series of hydroxyindole amides was rationally designed and synthesized. The most potent derivative was found to bind non-competitively with respect to ATP. (C) 2000 Elsevier Science Ltd. All rights reserved.