4-amino-3-(4-phenoxyphenyl)-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one derivatives and salts thereof
Inventors
Arabeyre, Catherine • Moliner, Patricia • BOISNARD, Sabine • Sallaberry, Damien • Perard, Serge • Roy, Sebastien
Interested in licensing this patent?
MTEC can help explore whether this patent might be available for licensing for your application.
Assignees
Member
Glycos Biomedical LtdWe are UK/US entity with a team based in Maryland and North Carolina comprising an expert team that has linked triggers to disease states including TBI and acute injuries associated with radiation, acute lung injury and infection.
We are UK/US entity with a team based in Maryland and North Carolina comprising an expert team that has linked triggers to disease states including TBI and acute injuries associated with radiation, acute lung injury and infection.
Publication Number
US-12624030-B2
Publication Date
2026-05-12
Expiration Date
Abstract
The present disclosure relates to 4-amino-3-(4-phenoxyphenyl)-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one variants or derivatives, and salts thereof, for use as agonists and antagonists. The disclosure further relates to compositions, methods of preparing, and methods of treatment.
Core Innovation
The disclosure relates to 4-amino-3-(4-phenoxyphenyl)-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one derivatives and salts thereof, including compounds defined by Formula I, Formula Ia, Formula Ib, Formula II, Formula IIa, Formula IIb, Formula III, Formula IV, and Formula V. The compounds are described as pharmaceutical compositions and medicaments comprising pharmaceutically acceptable excipients and at least one selected compound or salt thereof, with specified purity levels including about 90%, about 95%, about 98%, about 99%, and about 99.6%.
The disclosure also relates to synthetic routes for preparing acrylamide/acryloyl chloride-installed intermediates and related protected/deprotected derivatives, including preparation of Formula Ia and Formula Ib from Formula VIa/VIb and acryloyl chloride. In the disclosed routes, acid-based deprotection is used to access Formula VIa/VIb intermediates from Formula IX and/or Formula VII, and related transformation steps include base deprotection and chemistry involving triphenylphosphine and an azodicarboxylate.
The compounds are described in terms of being agonists or antagonists, with emphasis on Bruton tyrosine kinase (BTK) related activity. The background and disclosure scope frame BTK signaling and B-cell receptor signaling, and associate therapeutic targeting with autoimmune, inflammatory, cancer, and allergic indications.
Methods of treatment are described as administering an effective amount of the compound or salt to treat and/or prevent and/or inhibit and/or relieve disease, with autoimmune disorders and multiple sclerosis (MS) explicitly mentioned. Pharmaceutical dosage forms include capsule, tablet, and pill, and administration routes include oral, buccal, parenteral, nasal, topical, rectal, and inhalation.
Claims Coverage
The claim set includes five inventive feature groups directed to formula-defined compounds, preparation methods for Formula Ia and Formula Ib, a Formula II purity limitation, and a pharmaceutical composition including selected compounds and excipients.
Formula Ia compound with about 90% purity
A compound of Formula Ia, or a salt thereof, wherein the compound or salt thereof is about 90% pure.
Method preparing Formula Ia by reacting Formula VIa with acryloyl chloride
A method for preparing the compound of Formula Ia, or a salt of it, by reacting a compound of Formula VIa with acryloyl chloride.
Method further comprising preparing Formula VIa from Formula IX by acid-based deprotection
The method further comprises preparing a compound of Formula VIa from a compound of Formula IX by acid-based deprotection.
Formula Ib compound with about 90% purity
A compound of Formula Ib, or a salt thereof, wherein the compound or salt thereof is about 90% pure.
Method preparing Formula Ib by reacting Formula VIb with acryloyl chloride
A method prepares the compound of Formula Ib, or a salt thereof, by reacting a compound of Formula VIb with acryloyl chloride.
Method further comprising preparing Formula VIb from Formula VII by acid-based deprotection
The method further comprises preparing a compound of Formula VIb from a compound of Formula VII by acid-based deprotection.
About 99.6% pure compound of Formula II
A compound of Formula II, or salt thereof, wherein the compound or salt thereof is about 99.6% pure.
Pharmaceutical composition with pharmaceutically acceptable excipient and selected formula compound(s)
A composition comprising a pharmaceutically acceptable excipient and at least one compound chosen from Formula Ia, Formula Ib, Formula II, and Formula III, or salts thereof.
The claims cover formula-defined compounds of Formula Ia, Formula Ib, and Formula II with stated purity constraints, preparation methods using Formula VIa/VIb and acryloyl chloride with acid-based deprotection to form the intermediates, and a pharmaceutically acceptable composition comprising an excipient and selected formula compounds.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Treating multiple sclerosis (MS).
Treating autoimmune disorders including rheumatoid arthritis and lupus.
Treating autoimmune disorders.
Interested in licensing this patent?