1883301-82-3

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(1S)‐2,2‐difluorocyclopropane‐1‐carboxylic acid is used as a key intermediate in the synthesis of novel drugs and biologically active molecules. Its unique structure allows for the development of new compounds with potential medicinal applications.
Used in Agrochemicals:
(1S)‐2,2‐difluorocyclopropane‐1‐carboxylic acid is used as a building block in the design and production of agrochemicals, contributing to the development of effective and environmentally friendly pesticides and other agricultural products.
Used in Materials Science:
(1S)‐2,2‐difluorocyclopropane‐1‐carboxylic acid is used as a component in the development of new materials with specific properties, such as enhanced stability, reactivity, or selectivity, for various industrial applications.
Further research and development of (1S)‐2,2‐difluorocyclopropane‐1‐carboxylic acid could lead to new approaches for designing and producing important chemical compounds with potential medicinal and industrial applications.

Upstream product

• 694-34-8 1,1-difluoro-2-vinylcyclopropane 
• 260352-79-2 2,2-difluorocyclopropanecarboxylic acid butyl ester 
• 107873-03-0 2,2-difluorocyclopropane-1-carboxylic acid 

Downstream Products

• 1883301-82-3 (1R)-2,2-difluorocyclopropanecarboxylic acid 
• 1883299-62-4 ((S)-2,2-difluorocyclopropyl)-((1R,5S)-3-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone 
• 1883299-62-4 [(1R)-2,2-difluorocyclopropyl][(1R,5S)-3-{2-[(1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}-3,8-diazabicyclo[3.2.1]oct-8-yl]methanone 
• 1883301-82-3 (1S)-2,2-difluorocyclopropane-1-carboxylic acid 
• 509072-57-5 rac-(2,2-difluorocyclopropyl)methanol 
• 1374342-35-4 [4-(4-bromophenyl)piperazin-1-yl](2,2-difluorocyclopropyl)methanone 
• 1374342-34-3 [4-(4-bromophenyl)piperazin-1-yl](2,2-difluorocyclopropyl)methanone 
• 1426449-92-4 5-(2,2-difluorocyclopropyl)-3-(2,4-dimethyl-5-nitrophenyl)-1,2,4-oxadiazole 
• 1426448-55-6 N-{5-[5-(2,2-difluorocyclopropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide 

Relevant academic research and scientific papers

PREPARATION OF A PYRIMIDINYL-3,8-DIAZABICYCLO[3.2.1]OCTANYLMETHANONE DERIVATIVE AND SALT THEREOF

Methods for preparing ((S)-2,2-difluorocyclopropyl)-((1R,5S)-3-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]-octan-8-yl)methanone and intermediates used in the processes of preparation thereof.

AMINOPYRIMIDINYL DERIVATIVES

A compound of formula I: or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are each independently hydrogen or hydroxy; wherein R1 and R2 are not both hydroxy. Also provided are methods of treatment as Janus Kinase inhibitors and pharmaceutical compositions containing the compounds of the invention and combinations thereof with other therapeutic agents.

Large-Scale Cyclopropanation of Butyl Acrylate with Difluorocarbene and Classical Resolution of a Key Fluorinated Building Block

To address challenges in the preparation of a key building block containing a difluorocyclopropane moiety, we have developed a new protocol for difluorocarbene generation that relies on a Krapcho-type dealkylation of ethyl bromodifluoroacetate (EBDFA), an inexpensive and readily available fluorinated feedstock. Application of DoE and kinetic modeling was used to understand key reaction parameters and identify an optimal process. We report two variants of this procedure that offer different processing advantages and that have both been scaled successfully multiple times to deliver hundreds of kilograms of the resulting difluorocyclopropane. To access a single enantiomer of the target compound, we have also developed a classical resolution strategy and recycling protocol for the undesired enantiomer to replace previous chromatographic methods for separation.

Transition Metal-free gem-difluorocyclopropanation of Alkenes with CF3SiMe3?NaI System: a Recipe for Electron-deficient Substrates

Reaction of various electron-deficient alkenes, as well as functionalized styrene derivatives with CF3SiMe3?NaI system is studied. Relative reactivity of the substrates is established. It is shown that many α,β-unsaturated esters can

Neoplastic diseases and/or infectious diseases is useful bicyclic [...] derivatives (by machine translation)

The present invention relates to bicyclic tetrahydrothiazepine of formula (I), wherein R1 to R3, X1, X2 and R18 have the meaning as indicated in the description and claims. The invention further relates to pharmaceutical compositions comprising such compo

Dual Inhibition of TYK2 and JAK1 for the Treatment of Autoimmune Diseases: Discovery of ((S)-2,2-Difluorocyclopropyl)((1 R,5 S)-3-(2-((1-methyl-1 H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone (PF-06700841)

Cytokine signaling is an important characteristic of autoimmune diseases. Many pro-inflammatory cytokines signal through the Janus kinase (JAK)/Signal transducer and activator of transcription (STAT) pathway. JAK1 is important for the -common chain cytokines, interleukin (IL)-6, and type-I interferon (IFN) family, while TYK2 in addition to type-I IFN signaling also plays a role in IL-23 and IL-12 signaling. Intervention with monoclonal antibodies (mAbs) or JAK1 inhibitors has demonstrated efficacy in Phase III psoriasis, psoriatic arthritis, inflammatory bowel disease, and rheumatoid arthritis studies, leading to multiple drug approvals. We hypothesized that a dual JAK1/TYK2 inhibitor will provide additional efficacy, while managing risk by optimizing selectivity against JAK2 driven hematopoietic changes. Our program began with a conformationally constrained piperazinyl-pyrimidine Type 1 ATP site inhibitor, subsequent work led to the discovery of PF-06700841 (compound 23), which is in Phase II clinical development (NCT02969018, NCT02958865, NCT03395184, and NCT02974868).

HETEROCYCLIC COMPOUND

The present invention provide a heterocyclic compound having a HDAC inhibitory action, and useful for the treatment of autoimmune diseases and/or inflammatory diseases, graft versus host disease, cancers, central nervous diseases including neurodegenerative diseases, Charcot-Marie-Tooth disease and the like, and a pharmaceutical composition comprising the compound. The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.

PYRIMIDINE AND TRIAZINE DERIVATIVES AND THEIR USE AS AXL INHIBITORS

Compounds of the general formula(I): (I) processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

TETRAHYDROISOQUINOLINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS USEFUL FOR THE TREATMENT OF OBESITY AND DIABETES

The invention relates to new pyrrolidine derivatives of the formula wherein R1 to R6, n and m are as defined in the description and claims, to their use as medicaments, to methods for their therapeutic use and to pharmaceutical compositions containing them.

AMINOPYRIMIDINYL COMPOUNDS

A compound having the structure: or a pharmaceutically acceptable salt thereof, wherein X is N or CR, where R is hydrogen, deuterium, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl, heteroaryl, aryl(C1-C6 alkyl), CN, amino, alkylamino, dialkylamino, CF3, or hydroxyl; A is selected from the group consisting of a bond, C═O, —SO2—, —(C═O)NR0—, and —(CRaRb)q—, where R0 is H or C1-C4 alkyl, and Ra and Rb are independently hydrogen, deuterium, C1-C6 alkyl, C3-C6 cycloalkyl, aryl, aryl(C1-C6 alkyl), heteroaryl, (C1-C6 alkyl)heteroaryl, etc.; A′ is selected from the group consisting of a bond, C═O, —SO2—, —(C═O)NR0′, —NR0′(C═O)—, and —(CRa′Rb′)q—, where R0′ is H or C1-C4 alkyl, and Ra′ and Rb′ are independently hydrogen, deuterium, C1-C6 alkyl, C3-C6 cycloalkyl, aryl, aryl(C1-C6 alkyl), heteroaryl, (C1-C6 alkyl)heteroaryl, heteroaryl(C1-C6 alkyl), and heterocyclic(C1-C6 alkyl); Z is —(CH2)h— or a bond, where one or more methylene units are optionally substituted by one or more C1-C3 alkyl, CN, OH, methoxy, or halo, and where said alkyl may be substituted by one or more fluorine atoms; R1 and R1′ are independently selected from the group consisting of hydrogen, deuterium, C1-C4 alkyl, C3-C6 cycloalkyl, aryl, heteroaryl, aryl(C1-C6 alkyl), CN, etc., wherein said alkyl, aryl, cycloalkyl, heterocyclic, or heteroaryl is further optionally substituted with one or more substituents selected from the group consisting of C1-C6 alkyl, halo, CN, C1-C4 alkylamino, C3-C6 cycloalkyl, etc.; R2 is selected from the group consisting of hydrogen, deuterium, C1-C6 alkyl, C3-C6 cycloalkyl, halo, and cyano, where said alkyl may be substituted by one or more fluorine atoms; R3 is selected from the group consisting of hydrogen, deuterium, and amino; R4 is monocyclic or bicyclic aryl or monocyclic or bicyclic heteroaryl wherein said aryl or heteroaryl is optionally substituted with one or more substituents selected from the group consisting of C1-C6 alkyl, heterocycloalkyl, halo, C3-C6 cycloalkyl, etc., where said alkyl, cycloalkyl, alkoxy, or heterocycloalkyl may be substituted by one or more C1-C6 alkyl, halo, CN, OH, alkoxy, amino, —CO2H, —(CO)NH2, —(CO)NH(C1-C6 alkyl), or —(CO)N(C1-C6 alkyl)2, and where said alkyl may be further substituted by one or more fluorine atoms; R5 is independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, and hydroxyl; h is 1, 2 or 3; j and k are independently 0, 1, 2, or 3; m and n are independently 0, 1 or 2; and, q is 0, 1 or 2. Also provided are methods of treatment as Janus Kinase inhibitors and pharmaceutical compositions containing the compounds of the invention and combinations with other therapeutic agents.