Heterocyclic sulfonamide derivative and medicine containing same
Inventors
Kobayashi, Kaori • Suzuki, Tamotsu • Okuzumi, Tatsuya
Assignees
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Publication Number
US-10584116-B2
Publication Date
2020-03-10
Expiration Date
Abstract
Compounds of represented by formula (I): wherein each symbol is defined herein and pharmaceutically acceptable salts thereof exhibit TRPA1 antagonist activity and are useful as TRPA1 antagonists and the prophylaxis or treatment of diseases involving TRPA1.
Core Innovation
The invention relates to compounds represented by formula (I), or pharmaceutically acceptable salts thereof, including TRPA1 antagonist compounds. Ring A is a 6-membered, nitrogen-containing heterocycle substituted by 1 or 2 oxo groups, and Ar1 is selected from a C6-10 aryl group, a C1-9 heteroaryl group, or a C3-7 cycloalkyl group, each optionally having substituent(s).
The formula (I) further defines substituents R1 to R5 and X1/X2 with specific allowed forms and optional ring-forming relationships, including joining of R1 and R2 to form a nitrogen-containing ring, joining of R2 and R3 to form cycloalkene or cycloalkane, and joining of R4 and R5 to form cycloalkane. One of X1 and X2 is selected from Group A and the other is an alkyl group optionally having substituent(s), or hydrogen, and X1 and X2 are not hydrogen atoms at the same time.
Group A includes hydrogen and multiple linked fragments involving Cy and variants with oxygen-linked, sulfur-oxygen-linked, nitrogen-linked, and carbonyl-linked patterns, with defined integer ranges for n and m. A specific proviso applies when ring A has a pyridone skeleton, under which X1 is not a hydrogen atom. The document also states that the compounds are TRPA1 antagonists and includes examples with structural and characterization data.
Claims Coverage
The independent claim coverage centers on formula (I) compounds with one main scaffold and multiple structural inventive features, including the ring A oxo heterocycle, Ar1 scope, R1-R5 constraints, and the X1/X2 Group A framework. Dependent claims further narrow ring A, Ar1 substituent classes, and specific substituent choices, and include a therapeutic use claim.
Formula (I) with substituted ring A and Ar1
A compound represented by formula (I), or a pharmaceutically acceptable salt thereof, wherein ring A is a 6-membered, nitrogen-containing heterocycle substituted by 1 or 2 oxo groups, and Ar1 is a C6-10 aryl group, a C1-9 heteroaryl group, or a C3-7 cycloalkyl group, each optionally having substituent(s).
Variable substituents R1–R5 with optional ring formation
R1 is hydrogen or a C1-6 alkyl group optionally having substituent(s); R2 is hydrogen, a C1-6 alkyl group optionally having substituent(s), or a C2-6 alkenyl group optionally having substituent(s); R3, R4, and R5 are hydrogen or a C1-6 alkyl group; and R1 and R2, R2 and R3, or R4 and R5 are optionally joined to form the specified ring systems.
Group A selection for X1 and X2 with pyridone limitation
One of X1 and X2 is selected from Group A and the other is an alkyl group optionally having substituent(s), or hydrogen, with Group A including hydrogen and linked fragments involving Cy and variants; X1 and X2 are not hydrogen atoms at the same time, and when ring A is a pyridone skeleton, X1 is not a hydrogen atom.
Therapeutic administration for TRPA1-involved diseases
A method to treat a disease involving TRPA1 by administering an effective amount of a compound or pharmaceutically acceptable salt to a subject in need.
The claim coverage is concentrated on formula (I) compounds featuring an oxo-substituted 6-membered nitrogen-containing ring A, defined Ar1 options, constrained R1-R5 substituents with optional ring formation, and a Group A-based X1/X2 definition with a pyridone-specific restriction, together with therapeutic administration for TRPA1-involved diseases.
Stated Advantages
TRPA1 antagonist activity.
Prophylaxis and treatment of TRPA1-involved diseases.
Therapeutic indications across multiple disease categories, including pain-associated diseases, digestive tract diseases, lung diseases, bladder diseases, inflammatory diseases, dermatic diseases, and neurological diseases.
Documented Applications
Treatment of a disease involving TRPA1 by administering an effective amount of a compound or pharmaceutically acceptable salt to a subject in need.
TRPA1-involved diseases.
Use in prophylaxis and/or treatment of diseases involving TRPA1, including pain-associated diseases and functional dyspepsia and other gastrointestinal disorders, pulmonary diseases, dermatic diseases, inflammatory diseases, bladder diseases, and neurological diseases.
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