3-phenylpropylamine derivative
Inventors
Kageji, Hideaki • TSUKADA, Tomoharu • Tsuji, Takashi • Fujii, Masaya • Sugimoto, Yuuichi • TSUCHIYA, Yuto • Murakami, Keigo • Inoue, Hidekazu • Ebisawa, Masayuki • KUKI, Naoki • Hayashi, Noriyuki • Matsufuji, Tetsuyoshi • Asahi, Takashi • BANJO, Saki • Tsutsumi, Shinji • SHIMONAGA, Mariko • Igarashi, Takuya
Assignees
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Publication Number
US-12606533-B2
Publication Date
2026-04-21
Expiration Date
Abstract
The present invention aims to provide a novel compound having SF-1 antagonist activity and a polyfunctional molecule containing a moiety corresponding to the compound, particularly an SF-1 degrader. The present invention relates to a 3-phenylpropylamine derivative compound represented by the formula (1) and the like, and a polyfunctional molecule containing a moiety corresponding to the compound represented by the formula (1) and the like.
Core Innovation
The invention relates to stereochemically defined compounds selected from specified imidazo[4,5,1-ij]quinolin-1(2H)-yl and imidazo[1,5,4-de]quinoxalin-1(2H)-yl derived piperidine-2,6-dione structures, together with pharmaceutically acceptable salts. The selected molecules include stereochemical designations such as (3RS), (3R), (3S), and defined stereochemical centers, with extensive substituent variation and piperazine-1-carbonyl frameworks.
The disclosure further includes crystal forms of selected compounds as benzenesulfonate, ethanesulfonate, 10-camphorsulfonate, and salicylate salt forms. The crystal forms are characterized by powder X-ray diffraction peak positions reported as 2θ values measured using Cu Kα radiation, providing distinct powder X-ray diffraction fingerprints for each salt form.
The disclosure also includes representative compound examples and scaffold variants with different substituents and/or counterion forms. In addition, it presents SF-1-targeting compounds with SF-1 antagonist activity, SF-1 inhibitor activity, and SF-1 degrader concepts.
Claims Coverage
The consolidated claim coverage includes two independent claim themes: one directed to selected stereochemically defined compounds and pharmaceutically acceptable salts, and one directed to crystal forms of selected compounds as specific salt crystals. Across the claims, there are 3 principal inventive feature sets: defined compound identity, defined salt crystal form identity, and powder X-ray diffraction characterization.
Stereochemically defined imidazoquinoline piperidine-2,6-dione compounds
A compound selected from a specified group of stereochemically defined imidazo[4,5,1-ij]quinolin-1(2H)-yl and imidazo[1,5,4-de]quinoxalin-1(2H)-yl piperidine-2,6-dione structures, including (3RS), (3R), and (3S) variants and defined stereochemical centers, together with a pharmaceutically acceptable salt thereof.
Crystal forms of specified salt derivatives
A crystal of a compound selected from the group consisting of the defined stereochemically specified compounds presented as benzenesulfonate, ethanesulfonate, 10-camphorsulfonate, and salicylate salt forms.
Powder X-ray diffraction characterization
The crystal forms are characterized by powder X-ray diffraction peak positions (2θ) measured using Cu Kα radiation (λ = 1.54 Å), with distinct peak sets used to define individual crystal forms.
The claims primarily cover the defined stereochemically specified compound set, pharmaceutically acceptable salts thereof, and specific crystal salt forms characterized by powder X-ray diffraction peak positions under Cu Kα radiation.
Stated Advantages
Provides experimental evaluation and biological activity data for SF-1-targeting compounds, including binding inhibition, gene-expression downregulation, SF-1 degradation, and proliferation inhibition.
Reports in vivo antitumor efficacy in NSG xenograft models and related assays.
Provides characterization of crystal forms using powder X-ray diffraction peak sets measured with Cu Kα radiation.
Documented Applications
Treatment of hormone-related cancers or disorders, including castration-resistant prostate cancer, adrenocortical carcinoma, Leydig cell tumor, hormone-sensitive prostate cancer, breast cancer, Cushing's syndrome, and primary aldosteronism, by administering an effective amount of the compound or a pharmaceutically acceptable salt thereof.
In vivo antitumor efficacy evaluation using NSG xenograft models, including tumor growth inhibition in an NCI-H295R subcutaneous transplant model and xenograft prostate cancer models.
Pharmaceutical use for inhibiting SF-1 and for inducing degradation of SF-1.
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