93493-96-0

Upstream product

• 52784-37-9 2-carbomethoxy-2-cyclohexenone 
• 62344-14-3 (E)-methyl 3-oxo-6-octenoate 
• 105-45-3 acetoacetic acid methyl ester 
• 141-97-9 ethyl acetoacetate 
• 110874-83-4 methyl 3-oxo-6-octenoate 
• 84308-34-9 methyl 2-oxobicyclo<4.1.0>heptane-1-carboxylate 
• 15681-48-8 lithium dimethylcuprate 

Downstream Products

• 152564-11-9 (±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate 

Relevant academic research and scientific papers

The Discovery of (S)-1-(6-(3-((4-(1-(Cyclopropanecarbonyl)piperidin-4-yl)-2-methylphenyl)amino)-2,3-dihydro-1 H -inden-4-yl)pyridin-2-yl)-5-methyl-1 H -pyrazole-4-carboxylic Acid, a Soluble Guanylate Cyclase Activator Specifically Designed for Topical Ocular Delivery as a Therapy for Glaucoma

Soluble guanylate cyclase (sGC), the endogenous receptor for nitric oxide (NO), has been implicated in several diseases associated with oxidative stress. In a pathological oxidative environment, the heme group of sGC can be oxidized becoming unresponsive to NO leading to a loss in the ability to catalyze the production of cGMP. Recently a dysfunctional sGC/NO/cGMP pathway has been implicated in contributing to elevated intraocular pressure associated with glaucoma. Herein we describe the discovery of molecules specifically designed for topical ocular administration, which can activate oxidized sGC restoring the ability to catalyze the production of cGMP. These efforts culminated in the identification of compound (+)-23, which robustly lowers intraocular pressure in a cynomolgus model of elevated intraocular pressure over 24 h after a single topical ocular drop and has been selected for clinical evaluation.

CYCLOHEXEN-1-YL-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLIC ACID DERIVATIVES AND THE USE THEREOF AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS

The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacolo

Rh2(II)-catalyzed ester migration to afford 3 H-indoles from trisubstituted styryl azides

Rh2(II)-Complexes trigger the formation of 3H-indoles from ortho-alkenyl substituted aryl azides. This reaction occurs through a 4π-electron-5-atom electrocyclization of the rhodium N-aryl nitrene followed by a [1,2]-migration to afford only 3H-indoles. The selectivity of the migration is dependent on the identity of the β-styryl substituent.

Palladium-catalyzed intramolecular hydroalkylation of alkenyl- β-keto esters, α-aryl ketones, and alkyl ketones in the presence of Me 3SiCl or HCI

Reaction of 3-butenyl β-keto esters or 3-butenyl α-aryl ketones with a catalytic amount of [PdCl2(CH3CN)2] (2) and a stoichiometric amount of Me3SiCl or Me3SiCl/ CuCl2 in dioxane at 25-70°C formed 2-substituted cyclohexanones in good yield with high regioselectivity. This protocol tolerated a number of ester and aryl groups and tolerated substitution at the allylic, enolic, and cis and trans terminal olefinic positions. In situ NMR experiments indicated that the chlorosilane was not directly involved in palladium-catalyzed hydroalkylation, but rather served as a source of HCl, which presumably catalyzes enolization of the ketone. Identification of HCl as the active promoter of palladium-catalyzed hydroalkylation led to the development of an effective protocol for the hydroalkylation of alkyl 3-butenyl ketones that employed sub-stoichiometric amounts of 2, HCl, and CuCl2 in a sealed tube at 70°C.

Palladium-catalyzed intramolecular oxidative alkylation of 4-pentenyl β-dicarbonyl compounds

Reaction of 8-nonene-2,4-dione with a catalytic amount of [PdCl 2(CH3CN)2] (2; 5 mol%) and a stoichiometric amount of CuCl2 (2.5 equiv) at room temperature for 3 h led to oxidative alkylation and formation of 2-

Palladium-catalyzed cyclization of alkenyl β-keto esters in the presence of chlorotrimethylsilane

PdCl2(CH3CN)2 catalyzed the cyclization of alkenyl β-keto esters in the presence of a stoichiometric amount of SiMe3Cl to form 2-carboalkoxycyclohexanones in good yield with excellent regioselectivity.

Ring Opening of Cyclopropylketones Induced by Photochemical Electron Transfer

Depending on the substitution pattern of cyclopropylketones, the photochemically induced electron transfer of tertiary amines to cyclopropylketones leads either to the formation of 3-substituted cycloalkanones or to ring expanded products.

A new annulation method. Total syntheses of the sesquiterpenoids (+/-)-chiloscyphone and (+/-)-6-epi-chiloscyphone

The efficacy of a new annulation method, developed for the construction of functionalized bicyclic compounds, is illustrated by conversion of the β-keto esters 18 and 19 into the bicyclonon-1-enes 33 and 34, respectively, and by transformation of 2-methoxycarbonylcyclopentanone (20) into the bicyclonon-6-ene 38 and the bicyclodec-7-enes 48 and 51.Application of the method to total syntheses of the structurally unusual sesquiterpenoids (+/-)-chiloscyphone (16) and (+/-)-6-epi-chiloscyphone (17) is described.

Photochemical ring opening of cyclopropyl ketones induced by electron transfer

Irradiation of substituted bicyclo[n.1.0]alkan-2-ones at 254 nm in the presence of triethylamine and lithium perchlorate (LiClO4) can lead to cyclopropane ring opening with cleavage of the C(1)-C(n +2) (ring enlargement) or C(1)-C(n+3) bonds.