15690-55-8

Usage

Uses

Used in Fertility Treatment:
CIS-CLOMIPHENE HCL is used as a fertility aid for women to stimulate the release of hormones necessary for ovulation, thereby increasing the chances of conception.
CIS-CLOMIPHENE HCL is used as a fertility aid for men to increase testosterone production, which can improve sperm count and quality, enhancing the potential for successful fertilization.
Used in Pharmaceutical Industry:
CIS-CLOMIPHENE HCL is used as a therapeutic agent in the development of medications targeting infertility issues, providing an alternative to other fertility treatments and supporting reproductive health management.

InChI:InChI=1/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25-

Upstream product

• 540-38-5 p-Iodophenol 
• 53775-08-9 4-(2-chloro-1,2-diphenylvinyl)anisole 
• 100-37-8 2-(Diethylamino)ethanol 
• 72474-42-1 (Z)-(1-chloro-2-(4-methoxyphenyl)ethene-1,2-diyl)dibenzene 
• 140868-82-2 (E)-(2-bromo-1-chloro-2-iodovinyl)benzene 
• 72474-40-9 cis-1-Chloro-2-(4-hydroxyphenyl)-1,2-diphenylethylene 
• 869-24-9 2-chloro-N,N-diethylethylamine hydrochloride 
• 5720-07-0 4-methoxyphenylboronic acid 
• 98-80-6 phenylboronic acid 
• 536-74-3 phenylacetylene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 352-13-6 4-flourophenylmagnesium bromide 
• 35258-26-5 <4-<2-(diethylamino)ethoxy>phenyl>magnesium bromide 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 133157-86-5 (Z)-1-<4-(2-diethylaminoethoxy)phenyl>-1,2-diphenyl-1-penten-5-ol 
• 133157-93-4 (E)-1-<4-(2-diethylaminoethoxy)phenyl>-1,2-diphenyl-1-penten-5-ol 
• 7619-53-6 cis-clomiphene citrate 
• 7599-79-3 clomiphene citrate 

Relevant academic research and scientific papers

Stereoselective Nickel(II)-Catalyzed Addition of Aryl Grignards to Diphenylacetylene in the Synthesis of Zuclomiphene

Stereoselective synthesis of zuclomiphene was developed using nickel-catalyzed addition of 4-fluorophenylmagnesium bromide to 1,2-diphenylacetylene, followed by quenching with a chlorinating reagent. Since the aryl fluoride addition and chlorination reactions occur consecutively in one pot, the cis orientation of the two phenyl groups of 1,2-diphenylacetylene is conserved, leading to the highly selective synthesis of zuclomiphene. The use of the Grignard reagent resulted in the presence of bromide ions in the reaction mixture, which led to the formation of the bromo-analog of zuclomiphene. Alternative routes were then explored to overcome this issue to yield high-purity zuclomiphene.

Salts of Zuclomiphene

The present invention provides salts of zuclomiphene and crystalline forms thereof. Specific salts of zuclomiphene provided by the present invention include sulphate, phosphate, succinate, L-tartrate, tosylate, L-malate, maleate, malonate, fumarate, glycolate, and hemi-citrate. Also provided are pharmaceutical compositions including the zuclomiphene salts and crystalline forms thereof and the use of these salts in the treatment of a disorder selected from the group including osteoporosis, bone fractures, loss of bone mineral density (BMD) and hot flashes in a subject suffering therefrom.

TEMPO-Regulated Regio- and Stereoselective Cross-Dihalogenation with Dual Electrophilic X+ Reagents

A TEMPO catalyzed cross-dihalogenation reaction was established via redox-regulation of the otherwise complex system of dual electrophilic X+ reagents. Formally, the ICl, BrCl, I2 and Br2 were generated in-situ, which enabled high regio- or stereoselective access to a myriad of iodochlorination, bromochlorination and homo-dihalogenation products with a wide spectrum of functionalities. With its mild conditions and operational simplicity, this method could enable wide applications in organic synthesis, which was exemplified by divergent synthesis of two pharmaceuticals. Detailed mechanistic investigations via radical clock reaction, pinacol ring expansion and Hammett experiments were conducted, which confirmed the intermediacy of halonium ion. In addition, a dynamic catalytic model based on the versatile catalytic role of TEMPO was proposed to explain the selective outcomes.

Processes for the Preparation of Zuclomiphene and Intermediates Thereof

The present invention provides processes for the preparation of zuclomiphene, as well as intermediates useful in the preparation thereof. In particular, processes are provided for the carbometallation of diphenylacetylene with a compound of Formula (3) to afford either zuclomiphene or an intermediate which is converted to zuclomiphene.

COMPOSITION FOR CROSS TALK BETWEEN ESTROGEN RECEPTORS AND CANNABIONOID RECEPTORS

A composition for cross talk between estrogen receptors and cannabinoid receptors including a chelator and a receptor ligand is provided. A method of synthesizing the composition is also provided, and the composition may be further prepared in pharmaceutical formulations or kits for therapy or molecular imaging.

CLOMIPHENE SYNTHESIS USING A SINGLE SOLVENT

The present invention provides a one-pot method for synthesizing clomiphene (a mixture of the isomers cis-clomiphene and trans-clomiphene) utilizing a single solvent. In a preferred embodiment, the single solvent is dichloromethane (DCM, also known as methylene chloride). The present invention provides an improved method for synthesizing clomiphene and purifying clomiphene isomers.

Methods for Determining the Oncogenic Condition of Cell, Uses Thereof, and Methods for Treating Cancer

The invention relates to methods for detecting the oncogenic condition of cells, including step where the amount of the OCDO compound in said cells is measured, and to the uses thereof. The invention further relates to OCDO inhibitors for use in methods for treating cancer.

Stereospecific synthesis of clomiphene and tamoxifen via stannylcupration of diphenylacetylene

Stereospecific trans-stannylcupration of diphenylacetylene affords a 1,2-dimetallostilbene which may be elaborated into either Clomiphene or Tamoxifen through palladium-catalyzed coupling with an aryl iodide.