Benzodiazepine derivatives as RSV inhibitors
Inventors
SHOOK, Brian C. • Kim, In Jong • Blaisdell, Thomas P. • Yu, Jianming • Panarese, Joseph D. • Or, Yat Sun
Assignees
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Publication Number
US-12297209-B2
Publication Date
2025-05-13
Expiration Date
Abstract
The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit Respiratory Syncytial Virus (RSV). The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from RSV infection. The invention also relates to methods of treating an RSV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.
Core Innovation
The invention relates to a pharmaceutical composition comprising a compound represented by a formula, or a pharmaceutically acceptable salt thereof, wherein R4 is substituted with two substituents. Each substituent is independently selected from CH3, CN, fluoro, chloro, CH3O—, CH3C(O)—, CH3OCH2—, CH3OCH2CH2O—, —CF3, and CF3O—. The disclosed compositions are defined by the substitution pattern on R4 using the listed functional groups, with chemical structure depictions illustrating substituted aromatic/heteroaromatic embodiments and specific R4 substitution patterns.
The disclosure also describes substituted heteroaromatic compounds and related intermediates across multiple example series, including morpholine-containing, hydrazide/hydrazine/amide-containing, oxadiazole-linked, diazepinone, and benzo[e][1,4]diazepin derivatives. Example sets include variations such as fluorinated, cyano, trifluoromethyl, chloro, methoxy, methoxymethyl, and aryl or heteroaryl substituents, with some examples isolated as enantiomers or characterized as racemic or diastereomeric mixtures.
The examples support a common heterocyclic core with variation in substituents, stereochemistry, and heteroaryl frameworks, together with characterization by ESI-MS and 1H NMR. Dependent claim language further ties the R4 substitution pattern to depicted chemical structures, including particular fluorinated selections such as —CF3 and cyclopropyl/fluorinated structures, and one dependent claim frames the composition for treating human respiratory syncytial virus (RSV).
Claims Coverage
The claim set centers on one independent pharmaceutical composition claim with inventive features directed to a compound formula and an R4 position substituted with two independently selected groups from a defined functional-group set. Dependent claims further narrow the R4 substitution pattern by reference to depicted structures and fluorinated choices, and one dependent claim specifies treatment of human respiratory syncytial virus (RSV).
Pharmaceutical composition with defined R4 double substitution set
A pharmaceutical composition comprising a compound represented by the formula, or a pharmaceutically acceptable salt thereof, wherein R4 is substituted with two substituents, each independently selected from CH3, CN, fluoro, chloro, CH3O—, CH3C(O)—, CH3OCH2—, CH3OCH2CH2O—, —CF3, and CF3O—.
Specific fluorinated substituent choice for R4
A pharmaceutical composition wherein one substituent is —CF3 or a specified cyclopropyl/fluorinated structure shown in the provided image.
R4 structure tied to depicted images
A pharmaceutical composition wherein R4 has the structure shown in the first image and is further substituted by one selected group shown in the second image.
R4 substitution pattern defined by depicted chemical structure
A pharmaceutical composition wherein one substituent has the substitution pattern shown in the provided chemical structure images, including N/O presence.
Method of treating human respiratory syncytial virus
A method for treating human respiratory syncytial virus (RSV) by administering a therapeutically effective amount of the pharmaceutical composition to a human subject who needs such treatment.
Overall, the claims define a pharmaceutical composition by an R4 disubstitution pattern limited to a specified set of small functional groups, with dependent claims narrowing the substituent identity through depicted structures and fluorinated options. One dependent claim further limits the use to treating human RSV by administration of a therapeutically effective amount.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Method for treating human respiratory syncytial virus (RSV) by administering a therapeutically effective amount of the pharmaceutical composition to a human subject who needs such treatment.
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