922727-92-2

Basic information

• Product Name: (1R,2R,4R)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid
• Synonyms: (1R,2R,4R)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid;Cyclopentanecarboxylic acid, 2-[(5-hexen-1-ylmethylamino)carbonyl]-4-hydroxy-, (1R,2R,4R)-;(1R,2R,4R)-2-[(5-Hexen-1-ylmethylamino)carbonyl]-4-hydroxycyclopentanecarboxylic acid;(1R,2R,4R)-2-(Hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentanecarboxylic acid
• CAS NO: 922727-92-2
• Molecular Formula: C₁₄H₂₃NO₄
• Molecular Weight: 269.33672
• EINECS: -0
• Mol File: 922727-92-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,2R,4R)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,4R)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid(922727-92-2)
• EPA Substance Registry System: (1R,2R,4R)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid(922727-92-2)

Safety Data

• Hazardous Substances Data: 922727-92-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2R,4R)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid is used as a pharmaceutical compound for its potential medicinal properties. The unique structure and configuration of the compound may offer specific biological activities, making it a candidate for drug development, particularly in the areas of therapeutic intervention and treatment of various diseases.
Used in Chemical Industry:
In the chemical industry, (1R,2R,4R)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid may serve as a key intermediate in the synthesis of other complex organic molecules. Its carboxylic acid and carbamoyl functional groups can participate in various chemical reactions, such as esterification, amidation, and condensation, enabling the creation of a wide range of chemical products with diverse applications.

Upstream product

• 28269-02-5 cis-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) 
• 67885-98-7 (1R,2R)-4-hydroxycyclopentane-1,2-dicarboxylic acid 
• 862259-02-7 trans-(3R,4R)-3,4-bis(methoxycarbonyl)cyclopentanol 
• 862175-17-5 N-methylhex-5-en-1-amine hydrochloride 
• 862174-60-5 (1R,4R,5R)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid 
• 55863-02-0 N-methylhex-5-en-1-amine 
• 922520-05-6 2,2,2-trifluoro-N-(hex-5-enyl)-N-methylacetamide 
• 2695-47-8 6-Bromo-1-hexene 
• 1027355-52-7 3-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid hex-5-enyl-methylamide 
• 862174-98-9 (1R,4R,5R)-N-(hex-5-en-1-yl)-N-methyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide 

Downstream Products

• 922727-93-3 (1R,2S)-1-{[(1R,2R,4S)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester 

Relevant articles and documents

Toward the Synthesis of Fluorinated Analogues of HCV NS3/4A Serine Protease Inhibitors Using Methyl α-Amino-β-fluoro-β-vinylcyclopropanecarboxylate as Key Intermediate

Synthesis of fluorocyclopropyl building blocks, which constitute the core of various therapeutic agents against the hepatitis C virus, is described. The relevant methyl α-amino-β-fluoro-β-vinylcyclopropanecarboxylate has been used as a key intermediate for the total synthesis of a fluorinated analogue of Simeprevir (TMC 435), a HCV NS3/4A protease inhibitor.

Macrocylic Inhibitors of Hepatitis C Virus

Compounds of the formula I: and N-oxides, salts, and stereoisomers thereof wherein A is OR1, NHS(═O)pR2; wherein; R1 is hydrogen, C1-C6alkyl, C0-C3alkylenecarbocyclyl, C0-C3alkylene-heterocyclyl;R2 is C1-C6alkyl, C0-C3alkylenecarbocyclyl, C0-C3alkyleneheterocyclyl;p is independently 1 or 2;n is 3, 4, 5 or 6; — denotes an optional double bond;L is N or CRz; Rz is H or forms a double bond with the asterisked carbon;Rq is H or when L is CRz, Rq can also be C1-C6alkyl;Rr is quinazolinyl, optionally substituted with one two or three substituents each independently selected from C1-C6 alkyl, C1-C6alkoxy, hydroxyl, halo, haloC1-C6alkyl, amino, mono- or dialkylamino, mono- or dialkylaminocarbonyl, C1-C6alkyl-carbonylamino, C0-C3alkylenecarbocyclyl and C0-C3 alkyleneheterocyclyl;R5 is hydrogen, C1-C6alkyl, C1-C6alkoxyC1-C6alkyl or C3-C7cycloalkyl;R6 is hydrogen, C1-C6alkyl, C1-C6alkoxy, C0-C3alkylenecarbocyclyl, C0-C3alkylene-heterocyclyl, hydroxy, bromo, chloro or fluoro have utility in the treatment or prophylaxis of flaviviral infections such as HCV

PYRIMIDINE SUBSTITUTED MACROCYCLIC HCV INHIBITORS

Compounds of the Formula (I) including a stereoisomer thereof, or an N-oxide, a pharmaceutically acceptable addition salt, or a pharmaceutically acceptable addition solvate thereof; useful as HCV inhibitors; processes for preparing these compounds as well as pharmaceutical compositions comprising these compounds as active ingredient.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of Formula (I) and the salts and stereoisomers thereof, wherein each dashed line (represented by - - - - -) represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1 -6alkyl, C3 -7cycloalkyl; n is 3, 4, 5, or 6; R4 is C1-6alkyl or C3-7cycloalkyl; R5 is hydrogen, halo, C1-6alkyl, hydroxy, C1 -6alkoxy, polyhaloC1 -6alkyl; R6 is hydrogen, C1-6alkoxy, mono- or diC1 -6alkylamino; or R5 and R6 may form a 5- or 6-membered unsaturated or partially unsaturated ring, optionally co mprising one or two selected from O, N and S; R7 is hydrogen; C3-7cycloalkyl optionally subst ituted with C1-6alkyl; or C1-6alkyl optionally subst ituted with C3 -7cycloalkyl; R8 is C3-7cycloalkyl optionally subst ituted with C1 -6alkyl; C1 -6alkyl optionally substituted with C3-7cycloalkyl; or -NR8aR8b; R8a and R8b are C1-6alkyl, or both may form a 5- or 6-membered saturated heterocyclic ring; pharmaceut ical compositions containing compounds (I) and processes for preparing compounds (I).

POLYMORPHIC FORMS OF A MACROCYCLIC INHIBITOR OF HCV

Provided are crystalline forms of the compound of formula (I), which is a macrocyclic inhibitor of HCV, processes for the preparation thereof, and pharmaceutical compositions comprising these crystalline forms.

HCV INHIBITING MACROCYCLIC PHOSPHONATES AND AMIDOPHOSPHATES

Inhibitors of HCV replication of Formula (I) the /V-oxides, salts, and stcreochcmically isomeric forms thereof; pharmaceutical compositions containing compounds (1) and processes for preparin compounds (I). The side chain R2 is an amidophosphate or a phosphonate group and X, R1, R3, E and n are as defined in the application.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers thereof, wherein X is N, CH and where X bears a double bond it is C; R1 is -OR5, -NH-SO2R6; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, or C3-7cycloalkyl; R4 is isoquinolinyl optionally substituted with one, two or three substituents each independently selected from C1-6alkyl, C1-6alkoxy, hydroxy, halo, polyhalo- C1-6alkyl, polyhaloC1-6alkoxy, amino, mono- or diC1-6alkylamino, mono- or DiC1-6alkylaminocarbonyl, C1-6alkylcarbonyl-amino, aryl, and Het; n is 3, 4, 5, or 6; each dashed line (represented by ) represents an optional double bond; R5 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R6 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; each aryl is phenyl optionally substituted with one, two or three substituents; and each Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms each independently selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl; R4 is aryl or Het; n is 3, 4, 5, or 6; R5 is halo, C1-6alkyl, hydroxy, C1-6alkoxy, phenyl, or Het; R6 is C1-6alkoxy, or dimethylamino; R7 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R8 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents ; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.

MACROCYLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I), and the N-oxides, salts, and stereoisomers thereof, wherein each dashed line represents an optional double bond; X is Ν, CH and where X bears a double bond it is C; R1a and R1b are hydrogen, C3-7cycloalkyl, aryl, Het, C1-6alkoxy, C1-6alkyl optionally substituted with halo, C1-6alkoxy, cyano, polyhaloC11-6alkoxy, C3-7cycloalkyl, aryl, or with Het; or R1a and R1b together with the nitrogen to which they are attached form a 4 to 6 membered heterocyclic ring which may be optionally substituted; L is a direct bond, -O- , -O-C1-4alkanediyl-, -O-CO-, -O-C(=O)-ΝR5a - or -O -C(=O)-NR5a-C1-4alkanediyl-; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl, amino, mono- or diC1-6alkylamino; R4 is aryl or a saturated, a partially unsaturated or completely unsaturated 5 or 6 membered monocyclic or 9 to 12 membered bicyclic heterocyclic ring system wherein said ring system contains one nitrogen, and optionally one to three additional heteroatoms selected from O, S and N, and wherein the remaining ring members are carbon atoms; wherein said ring system may be optionally substituted; n is 3, 4, 5, or 6; p is 1 or 2; aryl is phenyl, naphthyl, indanyl, or 1,2,3,4-tetrahydronaphthyl, each of which may be optionally substituted with one, two or three substituents; and Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from N, O and S , being optionally condensed with a benzene ring, and wherein Het may be optionally substituted with one, two or three substituents; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I).