123536-66-3

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
(1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one is used as an intermediate in organic synthesis for the production of various drugs and complex organic molecules. Its unique structural features and reactivity make it an important tool for chemists in the development of new chemical entities or in the modification of existing compounds for improved biological activity.

Upstream product

• 5708-19-0 (1S)-3-cyclohexenecarboxylic acid 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 
• 116733-45-0 3-<(1R)-3-Cyclohexen-1-ylcarbonyl>-1,3-oxazolidin-2-one 
• 5709-98-8 (R)-cyclohex-3-enecarboxylic acid 
• 67976-82-3 (1S)-3-cyclohexene-1-carboxylic acid (R)-(+)-α-methylbenzylamine salt 
• 6493-77-2 (S)-(-)-methyl 3-cyclohexene-1-carboxylate 
• 102096-64-0 (S)-Cyclohex-3-enecarboxylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 

Downstream Products

• 123453-95-2 (1S,5S)-(-)-5-(hydroxymethyl)-2-cyclohexen-1-ol 
• 68295-80-7 (1S,5S)-5-Hydroxy-cyclohex-3-enecarboxylic acid methyl ester 
• 126640-65-1 3R-Hydroxycyclohex-4-en-1S-carboxylate 
• 70552-71-5 (5S)-5-<(1-ethoxyethoxy)methyl>-2-cyclohexen-1-one 
• 70552-73-7 (5S,6R,1'Z)-5-<(1-ethoxyethoxy)methyl>-6-(3'-methyl-1'-butenyl)-2-cyclohexen-1-one 
• 70552-73-7 (5S,6R)-5-(1-Ethoxy-ethoxymethyl)-6-((E)-3-methyl-but-1-enyl)-cyclohex-2-enone 
• 84162-00-5 (1S,5S,6R,1'Z)-5-<(1-ethoxyethoxy)methyl>-6-(3'-methyl-1'-butenyl)-1-vinyl-2-cyclohexen-1-ol 
• 123453-96-3 (5S,6S)-5-(1-Ethoxy-ethoxymethyl)-6-((1S,2R)-1-hydroxy-3-methyl-2-phenylselanyl-butyl)-cyclohex-2-enone 
• 123453-96-3 (5S,6S,1'R^*,2'R)-5-<(1-ethoxyethoxy)methyl>-6-(1'-hydroxy-3'-methyl-2'-phenylselenobutyl)-2-cyclohexen-1-one 
• 365997-31-5 (1S,3S,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid ethyl ester 
• 127308-75-2 (1R,5R)-5-(hydroxymethyl)-2-cyclohexen-1-ol 
• 4350-83-8 (R,S)-6-oxabicyclo[3.2.1]octan-7-one 
• 912273-65-5 N₁-(5-chloropyridin-2-yl)-N₂-{(1R,2R,4S)-4-(dimethylaminocarbonyl)-2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carboxamido]cyclohexyl}oxalamide p-toluenesulfonic acid 
• 480449-71-6 [14C]-Edoxaban tosylate 

Relevant academic research and scientific papers

Design, synthesis, and biological activity evaluation of a series of pleuromutilin derivatives with novel C14 side chains

In this work, according to the ‘me-too me-better’ design strategy, a peculiar side chain different from lefamulin at C14 position of pleuromutilin was introduced. A series of novel thioether pleuromutilin derivatives containing cyclohexane in the C14 chain was synthesized by ten-step synthesis reaction. All derivatives were characterized by Nuclear Magnetic Resonance (NMR) and High Resolution Mass Spectrometer (HRMS). Furthermore, majority of derivatives displayed moderate antibacterial activity in vitro. However, the compound 2C and 2J exhibited comparable or superior antibacterial activity to lefamulin. The summarized structure-activity relationship not only made the variety of pleuromutilin derivatives more diverse, but also provided new ideas for its design and development.

Preparation method of edoxaban tosylate and isomers thereof

The invention discloses a preparation method of edoxaban tosylate and isomers thereof. By taking a compound (I) and a compound (II) as starting materials, the method can be used to prepare any one ofhigh-purity edoxaban tosylate (1S, 2R, 4S), edoxaban tosylate enantiomers (1R, 2S, 4R), edoxaban tosylate epimers (1R, 2R, 4S) and edoxaban tosylate epimers (1S, 2S, 4R). Effective guarantee is provided for process research and quality control of the edoxaban tosylate bulk drug and related preparations, the preparation method is suitable for commercialization, the produced edoxaban tosylate bulk drug is high in purity and has great significance and practical value, and the production of the edoxaban tosylate bulk drug and the control of drug quality are facilitated.

Discovery of an Oxycyclohexyl Acid Lysophosphatidic Acid Receptor 1 (LPA1) Antagonist BMS-986278 for the Treatment of Pulmonary Fibrotic Diseases

The oxycyclohexyl acid BMS-986278 (33) is a potent lysophosphatidic acid receptor 1 (LPA1) antagonist, with a human LPA1 Kb of 6.9 nM. The structure-activity relationship (SAR) studies starting from the LPA1 antagonist clinical compound BMS-986020 (1), which culminated in the discovery of 33, are discussed. The detailed in vitro and in vivo preclinical pharmacology profiles of 33, as well as its pharmacokinetics/metabolism profile, are described. On the basis of its in vivo efficacy in rodent chronic lung fibrosis models and excellent overall ADME (absorption, distribution, metabolism, excretion) properties in multiple preclinical species, 33 was advanced into clinical trials, including an ongoing Phase 2 clinical trial in patients with lung fibrosis (NCT04308681).

Preparation method of edoxaban

The invention relates to a new preparation route and a new method for a p-toluenesulfonic acid edoxaban hydrate and intermediates thereof. The new method comprises the steps that a high-reactivity compound 109A4x is prepared; a compound 109C6x is prepared by using a new synthesizing method; new compounds 109E8-01, 109E9x and 109T7-01 are prepared; the p-toluenesulfonic acid edoxaban hydrate is prepared by using the intermediates. By using the new method and the new route, the reaction step of copious cooling is omitted, and dangerous elemental sulfur, high-risk n-butyllithium and high-risk azides are prevented from being used. In a word, by means of the method, the p-toluenesulfonic acid edoxaban hydrate and the key intermediates thereof are more easily and safely prepared at a lower coston an industrialization scale.

Method for preparing oxabicyclooctane compound

The invention relates to a method for preparing oxabicyclooctane compound, and the method comprises following steps: mixing 3-cyclohexene-1-formic acid shown in a formula (1), iodic acid and/or iodatewhich are shown in a formula (2), and iodide and acid (expect 3-cyclohexene-1-formic acid) which are shown in a formula (3) to obtain mixed liquor; and generating oxabicyclooctane compound shown in aformula (4) in the obtained mixed liquor; wherein the iodic acid can double as acid. (In the formula (2), A1 represents hydrogen atom or alkali metal.) (In the formula (3), A3 represents alkali metal.)

Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications

A general protocol is described for inducing enantioselective halolactonizations of unsaturated carboxylic acids using novel bifunctional organic catalysts derived from a chiral binaphthalene scaffold. Bromo- and iodolactonization reactions of diversely substituted, unsaturated carboxylic acids proceed with high degrees of enantioselectivity, regioselectivity, and diastereoselectivity. Notably, these BINOL-derived catalysts are the first to induce the bromo- and iodolactonizations of 5-alkyl-4(Z)-olefinic acids via 5-exo mode cyclizations to give lactones in which new carbon-halogen bonds are created at a stereogenic center with high diastereo- and enantioselectivities. Iodolactonizations of 6-substituted-5(Z)-olefinic acids also occur via 6-exo cyclizations to provide δ-lactones with excellent enantioselectivities. Several notable applications of this halolactonization methodology were developed for desymmetrization, kinetic resolution, and epoxidation of Z-alkenes. The utility of these reactions is demonstrated by their application to a synthesis of precursors of the F-ring subunit of kibdelone C and to the shortest catalytic, enantioselective synthesis of (+)-disparlure reported to date.

An efficient stereoselective synthesis of six stereoisomers of 3, 4-diaminocyclohexane carboxamide as key intermediates for the synthesis of factor Xa inhibitors

An efficient stereoselective route for the preparation of six stereoisomers of tert-butyl ((1R, 2S, 5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl)carbamate 1 starting from simple 3-cyclohexene-1-carboxylic acid has been described. Stereochemistry of the tit

METHOD OF PRODUCING IODOLACTONE COMPOUND

PROBLEM TO BE SOLVED: To provide a method of producing an iodolactone compound suitable to the industry in which the total amount of iodine (iodine, iodide and the like) used is reduced. SOLUTION: A method of producing an iodolactone compound represented by the formula (2) is characterized by reacting an unsaturated carboxylic acid represented by the formula (1), an iodide, a halogen oxo acid or salt thereof, and a second acid different from the halogen oxo acid, where compounds represented by the formulas (1) and (2) are as defined in the specification. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Discovery of N-[(1R,2S,5S)-2-{[(5-chloroindol-2-yl)carbonyl]amino}-5-(dimethylcarbamoyl)cyclohexyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride: A novel, potent and orally active direct inhibitor of factor Xa

In the early 1990's, we reported on the low-molecular selective fXa inhibitor DX-9065a having two amidino groups. However, it had poor oral bioavailability due to its strong basic amidino groups. To obtain fXa inhibitors with improved oral bioavailability

DIAMINE DERIVATIVES

A compound represented by formula (1):Q1-Q2-To-N(R1) -Q3-N(R2)-T1-Q4 [wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 represents the following group: (wherein Q5 is an alkylene group having 1 to 8 carbon atoms, or the like); and T0 and T1 are carbonyl groups or the like], a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after artificial valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.