cas 73505-48-3, METHYL-5-METHOXY-2-METHYLBENZOATE

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CYCLIC PENTAMER COMPOUNDS AS PROPROTEIN CONVERTASE SUBTILISIN/KEXIN TYPE 9 (PCSK9) INHIBITORS FOR THE TREATMENT OF METABOLIC DISORDER
The disclosure relates to inhibitors of PCSK9 useful in the treatment of cholesterol lipid metabolism, and other diseases in which PCSK9 plays a role, having the Formula (I):, or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, N-oxide, or tautomer thereof, wherein X1, R1, R2, R3, R4, R5, R6, R6', R7, R7', R8, R9, R9', R10, R11, R12, and n are described herein.
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Page/Page column 443-444

(2020/06/19)

PHENYL mTORC INHIBITORS AND USES THEREOF
The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 00345

(2018/05/27)

COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF ENHANCER OF ZESTE HOMOLOG 2 POLYPEPTIDE
The present disclosure relates to bifunctional compounds, which find utility as modulators of enhancer of zeste homolog 2 (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand which binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.
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Paragraph 1151-1154

(2018/07/15)

Method for constructing dihydrobenzofuran skeleton compound by oxidative coupling of two C-H bonds
The invention discloses a method for constructing a dihydrobenzofuran skeleton compound by oxidative coupling of two C-H bonds. According to the method, an intramolecular oxidative coupling reaction of carbon-hydrogen bonds is carried out on a carbon hydrogen bond C(sp)-H at the ortho-position of carboxyl on an aromatic ring in an alkoxy substituted benzoic acid derivative and a carbon-hydrogenbond C(sp) on an alkoxy group for constructing a carbon-carbon bond, and then the dihydrobenzofuran skeleton compound is obtained. The method provided by the invention has an important applicationvalue.
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Paragraph 0089; 0090; 0091

(2018/03/25)

PHENYL AMINO PIPERIDINE mTORC INHIBITORS AND USES THEREOF
The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 0385-0386

(2018/05/24)

PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS
Compounds of Formula (I), Formula (II), Formula (III), Formula (IV), Formula (V), Formula (VI), Formula (VII), Formula (VIII), and methods of use as lnterleukin-1 Receptor Associated Kinase (IRAK4) inhibitors are described herein.
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Page/Page column 186

(2019/01/10)

Structural development studies of pyrazoloketone-derived acetyl-CoA carboxylase inhibitors
Acetyl-CoA carboxylase (ACC) plays a key role in fatty acid homeostasis in humans, and inhibitors of ACC are expected to inhibit fatty acid biosynthesis and to activate fatty acid β-oxidation. Therefore, they are considered to be candidates for treatment of metabolic syndrome and related diseases. In this context, an upstream kinase of ACC, adenosine monophosphate-activated protein kinase (AMPK), has also recently emerged as a potential therapeutic target, because it phosphorylates and inactivates ACC. Here, we designed a fused molecule consisting of a pyrazoloketone-type ACC inhibitor and a recently discovered AMPK activator, aiming to develop a novel combined ACC inhibitor/AMPK activator to regulate fatty acid levels. The designed compound was prepared through a convergent synthetic route. This compound and its methyl ester analogue showed potent ACC2-inhibitory activity with IC50 values of 8.8 and 1.3 μM, respectively. Exomethylene derivatives, obtained from an unexpected side reaction during deprotection, also exhibited ACC2-inhibitory activity.
Okazaki, Shogo,Sakai, Taki,Ishikawa, Minoru,Hashimoto, Yuichi,Yamaguchi, Takao
p. 595 - 607
(2019/05/21)

METHOD FOR PREPARING PHENOLICS USING A CATALYST
The invention is directed to a method for preparing a phenolic compound comprising reacting a furanic compound with a dienophile in the presence of a catalyst comprising yttrium.
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Paragraph 10; 11; 12

(2017/07/14)

Synthesis, structure-activity relationships, and biological evaluation of a series of benzamides as potential multireceptor antipsychotics
In the present study, a series of benzamides, endowed with potent dopamine D2, serotonin 5-HT1A and 5-HT2A receptors properties, was synthesized and evaluated as potential antipsychotics. Among them, 3-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl)butoxy)-N-methylbenzamide (21) and its fluoro-substituted analogue (22) held the best pharmacological binding profiles. They not only presented potent activities for D2, 5-HT1A, and 5-HT2A receptors, but were also endowed with low activities for 5-HT2C, H1 receptors and hERG channels, suggesting a low propensity of inducing weight gain and QT prolongation. In animal models, compounds 21 and 22 reduced phencyclidine-induced hyperactivity with a high threshold for catalepsy induction. It thus provides potential candidates for further preclinical studies.
Yang, Feipu,Jiang, Xiangrui,Li, Jianfeng,Wang, Yu,Liu, Yongjian,Bi, Minghao,Wu, Chunhui,Zhao, Qingjie,Chen, Weiming,Yin, Jingjing,Zhang, Jian,Xie, Yuanchao,Hu, Tianwen,Xu, Mingshuo,Guo, Shuang,Wang, Zhen,He, Yang,Shen, Jingshan
supporting information
p. 3141 - 3147
(2016/06/13)

Asymmetric synthesis of (+)-17-: Epi -methoxy-kauran-3-one through tandem oxidative polycyclization-pinacol process
A synthesis of (+)-17-epi-methoxy-kauran-3-one, an O-methylated isomer of the natural diterpene 17-hydroxy-kauran-3-one, has been achieved. The strategy is based on a diastereoselective oxidative polycyclization-pinacol tandem process consisting of transforming a functionalized phenol into a compact and complex tetracycle, which represents the main core of kaurane family members. The synthesis also includes an enantioselective Yamamoto's allylation, a diastereoselective Ru-catalyzed hydrocyanation, a ring-closing metathesis and a reductive isomerization process as key steps. The structure of our synthetic substrate was determined through comparison with an O-methylated derivative of the natural compound.
Maertens, Ga?tan,Desjardins, Samuel,Canesi, Sylvain
supporting information
p. 6744 - 6750
(2016/07/21)

Ruthenium-Catalyzed Hydroarylation and One-Pot Twofold Unsymmetrical C?H Functionalization of Arenes
A methyl phenyl sulfoximine (MPS) is used as a directing group in the ruthenium-catalyzed intramolecular hydroarylation of alkene-tethered benzoic acid derivatives to afford dihydrobenzofurans and indolines in good to excellent yields. A one-pot, unsymmetrical, twofold C?H functionalization involving intramolecular C?C and intermolecular C?C/C?N bond formations is successfully demonstrated by using a single set of catalytic reaction conditions, which is unprecedented thus far. A novel isoquinolone-bearing dihydrobenzofuran is constructed through an unsymmetrical twofold C?H functionalization.
Ghosh, Koushik,Ramesh, E.,Rit, Raja K.,Sahoo, Akhila K.
supporting information
p. 7821 - 7825
(2016/07/07)

METHOD TO PREPARE PHENOLICS FROM BIOMASS
The present invention is directed to a method for preparing a final phenolic product from biomass comprising the steps of providing a furanic compound obtainable from biomass; reacting the furanic compound with a dienophile to obtain a phenolic compound; reacting the phenolic compound further to obtain the final phenolic product.
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Page/Page column 23

(2016/08/10)

Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates
Described is the development of a highly efficient 2πdisrotatory ring-opening aromatization sequence using bicyclo[3.1.0]hexan-2-ones. This unprecedented transformation efficiently proceeds under thermal conditions and allows facile construction of uniquely substituted and polyfunctionalized benzoates. In the presence of either amines or alcohols formation of substituted anilines or ethers, respectively, is achieved. Additionally, the utility of this method was demonstrated in a short synthesis of sekikaic acid methyl ester. Cracked open: A highly efficient thermal 2πdisrotatory ring-opening aromatization sequence of bicyclo[3.1.0]hexan-2-ones is described. The transformation proceeds in sulfolane to give uniquely substituted benzoates. In the presence of either amines or alcohols, formation of substituted anilines or ethers, respectively, is achieved.
Feierfeil, Johannes,Grossmann, Adriana,Magauer, Thomas
supporting information
p. 11835 - 11838
(2015/10/05)

ARYL AND HETEROARYL FUSED LACTAMS
This invention relates to compounds of general formula (I) in which R1, R2, U, V, L, M, R5, m, X, Y and Z are as defined herein, and the pharmaceutically acceptable salts thereof, to pharmaceutical compositions comprising such compounds and salts, and to methods of using such compounds, salts and compositions for the treatment of abnormal cell growth, including cancer.
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Paragraph 0989; 0990

(2014/07/08)

Asymmetric synthesis of the main core of kaurane family members triggered by an oxidative polycyclization-pinacol tandem process
Polycyclization processes represent expeditious routes used in both nature and the laboratory to produce complex polycyclic molecules. A new stereoselective oxidative variant of such a polycyclization has been developed in which the cascade is triggered by a phenol dearomatization and is concluded by a pinacol transposition. This unprecedented avenue combines the synthetic power of a polycyclization and a transposition in tandem and enables the rapid formation of the tetracyclic main core of kaurane diterpenes containing several asymmetric and quaternary carbon centers in a single step from a simple phenol derivative.
Desjardins, Samuel,Maertens, Ga?tan,Canesi, Sylvain
supporting information
p. 4928 - 4931
(2015/04/27)

PIPERIDINE AMIDES AS MODULATORS OF THE GHRELIN RECEPTOR
Compounds of formula (I) or pharmaceutically acceptable salts thereof, are useful for the treatment of diabetes and obesity.
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Page/Page column 94

(2011/10/13)

NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL AS ANTI-DIABETIC AGENTS
Novel compounds of the structural formula (I) are activators of AMP-protein kinase and are useful in the treatment, prevention and suppression of diseases mediated by the AMPK-activated protein kinase. The compounds of the present invention are useful in the treatment of Type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, hypercholesterolemia, and hypertension.
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Page/Page column 37

(2010/04/25)

NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL ANTI-DIABETIC AGENTS
Novel compounds of the structural formula (I) are activators of AMP-protein kinase and are useful in the treatment, prevention and suppression of diseases mediated by the AMPK-activated protein kinase. The compounds of the present invention are useful in the treatment of Type 2 diabetes, hyperglycemia, Metabolic Syndrome, obesity, hypercholesterolemia, and hypertension
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Page/Page column 78

(2010/05/13)

CARBOXYLIC ACID-CONTAINING COMPOUNDS, DERIVATIVES THEREOF, AND RELATED METHODS OF USE
Compounds that modulate gamma secretase (e.g., alter the cleavage pattern of gamma secretase) are described herein. Also disclosed are pharmaceutical compositions, methods of modulating the activity of gamma secretase, and methods of treating Alzheimer's Disease using the compounds described herein.
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Page/Page column 171-172

(2010/12/26)

NOVEL PYRAZOLONE-DERIVATIVES AND THEIR USE AS PD4 INHIBITORS
The compounds of formula (1) wherein R1 represents a phenyl derivative of formulae (a), (b) or (c) R10 is 1-3C-alkyl and R11 is 1-3C-alkyl, or R10 and R11 together with the carbon atom, to which they are bonded, form a spiro-linked 3-, 4-, 5- or 6-membered hydrocarbon ring, A is C(O) or S(O)2, and R12 is phenyl, naphthalenyl, pyridinyl, quinolinyl, isoquinolinyl, quinoxalinyl, 1,6-naphthyridinyl, 1,8-naphthyridinyl, indolyl, phenyl substituted by R13, R14, R15 and R16, pyridinyl substituted by R17 and R18, naphthalenyl substituted by R19 and R20, quinolinyl substituted by R21 or indolyl substituted by R22, are novel effective inhibitors of the type 4 phosphodiesterase.
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Page/Page column 109

(2010/06/15)

FUSED HETEROCYCLIC COMPOUND
The present invention provides a fused heterocyclic compound having a tyrosine kinase inhibitory action, which is represented by the formula: wherein R1 is a hydrogen atom, a halogen atom, or an optionally substituted group bonded via a carbon atom, a nitrogen atom or an oxygen atom; R2 is a hydrogen atom, or an optionally substituted group bonded via a carbon atom or a sulfur atom, or R1 and R2, or R2 and R3 are optionally bonded to each other to form an optionally substituted ring structure; R3 is a hydrogen atom or an optionally substituted aliphatic hydrocarbon group, or R3 is optionally bonded to the carbon atom on ring A to form an optionally substituted ring structure; ring A is an optionally substituted benzene ring; and ring B is (i) an optionally substituted fused ring, or (ii) a pyridine ring having optionally substituted carbamoyl (the pyridine ring is optionally further substituted).
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Page/Page column 67

(2009/10/01)

Tandem annulation strategy for the convergent synthesis of benzonaphthopyranones: total synthesis of chartarin and O-methylhayumicinone
A Hauser-initiated tandem annulation has been developed for the rapid regiospecific synthesis of benzonaphthopyranones via formation of two rings in one-pot operation. This strategy has been generalized with benzonaphthopyranones 26, 29, 32, and 35. It has also been employed in a short synthesis of chartarin (3) and O-methylhayumicinone (67).
Ray, Sutapa,Patra, Asit,Mal, Dipakranjan
p. 3253 - 3267
(2008/09/19)

Enantioselective synthesis of the dimeric pyranonaphthoquinone core of the cardinalins using a late-stage homocoupling strategy
The enantioselective synthesis of a dimeric pyranonaphthoquinone closely related to the cardinalins is described. Whilst attempts to effect a double Hauser-Kraus annulation of enone 5 were unsuccessful using both bis-phthalide 4 and bis-sulfone 21, a sing
Sperry, Jonathan,Gibson, Jennifer S.,Sejberg, Jimmy J. P.,Brimble, Margaret A.
supporting information; experimental part
p. 4261 - 4270
(2009/02/07)

Design, synthesis, and evaluation of cyclic amide/imide-bearing hydroxamic acid derivatives as class-selective histone deacetylase (HDAC) inhibitors
A series of hydroxamic acid derivatives bearing a cyclic amide/imide group as a linker and/or cap structure, prepared during our structural development studies based on thalidomide, showed class-selective potent histone deacetylase (HDAC)-inhibitory activity. Structure-activity relationship studies indicated that the steric character of the substituent introduced at the cyclic amide/imide nitrogen atom, the presence of the amide/imide carbonyl group, the hydroxamic acid structure, the shape of the linking group, and the distance between the zinc-binding hydroxamic acid group and the cap structure are all important for HDAC-inhibitory activity and class selectivity. A representative compound (30w) showed potent p21 promoter activity, comparable with that of trichostatin A (TSA), and its cytostatic activity against cells of the human prostate cell line LNCaP was more potent than that of the well-known HDAC inhibitor, suberoylanilide hydroxamic acid (SAHA).
Shinji, Chihiro,Maeda, Satoko,Imai, Keisuke,Yoshida, Minoru,Hashimoto, Yuichi,Miyachi, Hiroyuki
p. 7625 - 7651
(2007/10/03)

3-AMINO-PYRAZOLO[3,4B]PYRIDINES USED AS INHIBITORS OF PROTEIN TYROSINE KINASES FOR TREATING ANGIOGENIC, HYPERPROLIFERATIVE OR NEURODEGENERATIVE DISEASES
The invention relates to compounds of general formula (I), in which R1 and R2 are described in the application, to the use of the compounds of general formula (I) as inhibitors of protein tyrosine kinases for treating various diseases, and to the compounds of general formulas (II) and (III) as intermediate compounds for producing compounds of general formula (I), in which X, R1a and R2a have the meanings as described in general formulas (II) and (III).
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Page/Page column 76

(2008/06/13)

ALPHA ARYL OR HETEROARYL METHYL BETA PIPERIDINO PROPANAMIDE COMPOUNDS AS ORL1-RECEPTOR ANTAGONIST
This invention provides the compounds of formula (I): or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof, wherein Ri and R2 independently represent a hydrogen atom or the like; R3 represents a hydrogen atom, or the like; R4 represents a hydrogen atom or the like; (formula II) represents one of the following or the like; R5 represents an aryl group having from 6 to 10 ring atoms or the like; X represents an oxygen atom, or the like; Y represents an oxgen atom or the like and n represents an integer 0, 1 or 2. These compounds have ORL1-receptor antagonist activity; and therefore, are useful to treat diseases or conditions such as pain, various CNS diseases etc.
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Page/Page column 99

(2010/02/14)

NOVEL AMINOBENZOPHENONE COMPOUNDS
The invention provides novel compounds according to formula I relates to compounds with the general formula I said compounds being useful, e.g. in the treatment of inflammatory, ophthalmic diseases or cancer.
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Page 175

(2010/02/10)

Convergent and rapid assembly of benzonaphthopyranone cores of chartreusin, chrymutasins and hayumicins
A new methodology for the rapid regiospecific synthesis of benzonaphthopyranones has been developed, on the basis of a tactical extension of the Hauser-Kraus annulation. The prowess of the methodology has been illustrated by a short synthesis of chartarin (22b) and a facile entry to the chrymutasin scaffold (26).
Mal, Dipakranjan,Patra, Asit,Roy, Haren
p. 7895 - 7898
(2007/10/03)

Vitamin D analogues
The invention concerns novel bi-aromatic compounds having the formula: which are analogs of vitamin D, the process of preparing them, as well as their use in pharmaceutical compositions in human or veterinary medicine, particularly in dermatology, cancer treatment, treatment of auto-immune diseases, and in organ or tissue transplants. Cosmetic compositions and methods of use are also included.
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Page column 86

(2010/02/05)

Photochemical and acid-catalyzed rearrangements of 4-carbomethoxy-4-methyl-3-(trimethylsilyl)-2,5-cyclohexadien-1-one
The synthesis of 4-carbomethoxy-4-methyl-3-(trimethylsilyl)-2,5-cyclohexadien-1-one (1) in 60% overall yield from benzaldehyde is described. Irradiation (366 nm) of 1 in benzene solution gave products of type A photorearrangement; e.g., diastereomers of the 4-(trimethylsilyl)- and 5-(trimethylsilyl)bicyclo[3.1.0]hex-3-en-2-ones 8 and 9. Bicyclohexenones 9a and 9b could not be isolated, but underwent acid-catalyzed protiodesilylative rearrangements on attempted chromatography (silica gel) to give a 1:1 mixture of (E)- and (Z)-4-(carbomethoxymethylmethylene)cyclopent-2-en-1-ones 12 and 13. Irradiation (366 nm) of either 12 or 13 resulted in photoisomerization to a photostationary state that was also a 1:1 mixture. Irradiation of 8a or 8b gave equivalent mixtures of phenols 14 and 15 by way of the type B oxyallyl zwitterion 17. The available experimental evidence suggests that both 9a and 9b undergo regiospecific photorearrangement to phenol 16 with no trace of 3-methyl-4-carbomethoxyphenol (19), the product of ipso substitution of the Me3Si group at C(4). Phenol 15 was isolated in 65% yield from the photoreaction of 1 in benzene with 20 equiv of CF3CO2H. The acid-catalyzed rearrangement of 1 to 3-carbomethoxy-4-methylphenol (21) occurs in 91% yield by way of CO2Me group rearrangement to C(3) to give the Me3Si-stabilized carbocation 23.
Schultz, Arthur G.,Antoulinakis, Evan G.
p. 4555 - 4559
(2007/10/03)

REACTIONS OF -CYCLOADDITION WITH THE PARTICIPATION OF CYCLOPROPENES AND DICOBALT HEXACARBONYL COMPLEXES OF ACETYLENES
The reaction of dicobalt hexacarbonyl complexes of acetylene and its phenyl and dimethyl derivatives with the methyl ester of 1-methyl-2-(trimethylsilyl)-1-cyclopropene-3-carboxylic acid with adsorption on a silica gel or NaX zeolite surface leads to the formation of a mixture of bicyclohex-2-en-4-one and tricyclo2,4>heptan-5-one derivatives, whereby the yields and the composition of products are dependent on the type of the adsorbent.It has been found that under the reaction conditions partial isomerization of the bicyclohex-2-en-4-one derivativ es into substituted phenols occurs.Action of anhydrous KF and crown-ether in acetonitrile on the bicyclohex-2-en-4-one derivatives in acetonitrile leads to protodesilylation.
Kireev, S.L.,Smit, V.A.,Ugrak, B.I.,Nefedov, O.M.
p. 2240 - 2246
(2007/10/02)

(Methoxyalkyl)thiazoles: A new series of potent, selective, and orally active 5-lipoxygenase inhibitors displaying high enantioselectivity
(Methoxyalkyl)thiazoles are novel 5-lipoxygenase (5-LPO) inhibitors that are neither redox agents nor iron chelators. Consideration of a hypothetical model of the enzyme active site led to this series which is exemplified by 1-[3(naphth-2-ylmethoxy)phenyl]-1-(thiazol-2-yl)propyl methyl ether (2d, ICI211965). 2d inhibits cell-free guinea pig 5-LPO activity, LTC4 synthesis in plasma free mouse macrophages, and LTB4 synthesis in rat and human blood (IC50s 0.1 μM, 8nM, 0.5 μM, and 0.4 μM, respectively) but does not inhibit the synthesis of cyclooxygenase products at concentrations up to 50 μM in macrophages and 100 μM in blood. 2d is orally active in rat (ex vivo ED50 10 mg/kg in blood taken in 1h after dosing). SAR studies show that high in vitro potency requires methoxy, thiazolyl, and naphthyl groups and depends critically on the substitution pattern. (Methoxyalkyl)thiazoles are chiral. Resolution of 1-methoxy-6-(naphth-2-ylmethoxy)-1-(thiazol-2-yl)indan (2j, ICl216800) shows that (+)-2j is 50-150-fold more potent than (-)-2j in in vitro assays. Thus, (methoxyalkyl)thiazoles are a new series of orally active, selective 5-LPO inhibitors and represent the first class of inhibitors in which inhibition is mediated by specific, enantioselective interactions with the enzyme.
Bird,Bruneau,Crawley,Edwards,Foster,Girodeau,Kingston,McMillan
p. 2176 - 2186
(2007/10/02)

A Synthetically Useful Conversion of Benzoic Acid Derivatives to 4-Alkylphenols and 4-Alkyl-3-carbalkoxyphenols
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Schultz, Arthur G.,Harrington, Roger E.,Macielag, Mark,Mehta, Parag G.,Taveras, Arthur G.
p. 5482 - 5484
(2007/10/02)

Synthesis of Aromatic Monoterpenyl Geranyl Ethers as Possible Insect Juvenile Hormon Mimics
Substituted phenyl geranyl (IX-XV, XXIV-XXVIII) and 7-methoxygeranyl ethers (XVI-XXIII, XXVIII) have been synthesised as possible juvenile hormon (JH) mimics.Out of these ethers only XVII, XVIII and XXIII show low JH activity.
Phadnis, A. P.,Nanda, B.,Patwardhan, Sarita A.,Gupta, A. S.
p. 1098 - 1102
(2007/10/02)