WO2014198880A1 - Composés 2-(2-aminophénoxy)-3-chloronaphthalène-1,4-diones ayant une activité agoniste des récepteurs des orexines de type 2 - Google Patents

Composés 2-(2-aminophénoxy)-3-chloronaphthalène-1,4-diones ayant une activité agoniste des récepteurs des orexines de type 2 Download PDF

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Publication number
WO2014198880A1
WO2014198880A1 PCT/EP2014/062349 EP2014062349W WO2014198880A1 WO 2014198880 A1 WO2014198880 A1 WO 2014198880A1 EP 2014062349 W EP2014062349 W EP 2014062349W WO 2014198880 A1 WO2014198880 A1 WO 2014198880A1
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Prior art keywords
phenyl
cycloalkyl
group
dione
chloronaphthalene
Prior art date
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PCT/EP2014/062349
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English (en)
Inventor
Montserrat Cano
Pedro Manuel GRIMA
Albert Palomer Benet
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Ferrer Internacional, S.A.
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Publication of WO2014198880A1 publication Critical patent/WO2014198880A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/88—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/94—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom

Definitions

  • the invention relates to novel 2-(2-aminophenoxy)-3-chloronaphthalene-1 ,4- dione compounds having orexin 2 receptor (OX2R) agonist activity.
  • the invention also relates to their manufacture, pharmaceutical compositions comprising them, and their use as medicaments.
  • treatment refers to the treatment of a disease or medical condition in a human patient which includes:
  • asymmetric 2,3-dichloronaphthalene-1 ,4-diones (II, R 7 — C— C— R 8 fragment ⁇ R 10 — C— C— R 9 fragment) can produce mixtures of final products of formula (I). These mixtures can be separated on the basis of the physico- chemical differences of the constituents, in a known manner, into the pure final products, for example by chromatography, distillation, fractional crystallization, or by the formation of a salt if appropriate or possible under the circumstances.
  • Another aspect of the present invention is to provide a pharmaceutical composition containing a compound of formula (I) of the present invention or pharmaceutically acceptable salts, in association with therapeutically inert excipients.
  • FBS Fetal Bovine serum
  • examples 2-34 were obtained by reacting the appropriate 2,3-dichloro-1 ,4-naphtoquinone compound with the appropriate 2-aminophenol compound. lUPAC names, yields and analytical data are summarized in table 2.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention porte sur un composé de formule (I), dans laquelle R2 à R10 représentent des significations différentes, et sur leurs sels pharmaceutiquement acceptables. L'invention porte également sur des voies de synthèse pour la préparation des composés de formule (I), sur des compositions pharmaceutiques les comprenant, sur leur utilisation comme médicaments, sur leur utilisation comme substances actives thérapeutiques permettant le traitement d'affections à médiation par l'agonisme des récepteurs des orexines de type 2 et sur leur utilisation comme substances actives thérapeutiques permettant le traitement de la narcolepsie, de l'hypersomnie, de l'insomnie nocturne, de la dépression, de l'apnée du sommeil et du décalage horaire, pour favoriser l'état de veille et le réveil après anesthésie et pour la prévention de l'obésité due à un régime alimentaire.
PCT/EP2014/062349 2013-06-14 2014-06-13 Composés 2-(2-aminophénoxy)-3-chloronaphthalène-1,4-diones ayant une activité agoniste des récepteurs des orexines de type 2 WO2014198880A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP13172105 2013-06-14
EP13172105.2 2013-06-14

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WO2014198880A1 true WO2014198880A1 (fr) 2014-12-18

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Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3029024A1 (fr) * 2014-12-02 2016-06-08 Ferrer Internacional, S.A. Composés de 2-(2-aminophénoxy)-3-chloronaphthalène-1,4-dione présentant une activité d'agoniste du récepteur d'orexine 2
US9676747B2 (en) 2011-12-21 2017-06-13 Novira Therapeutics, Inc. Hepatitis B antiviral agents
WO2017135306A1 (fr) 2016-02-04 2017-08-10 Takeda Pharmaceutical Company Limited Composé de pipéridine substituée et son utilisation
US9873671B2 (en) 2014-01-16 2018-01-23 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US9884818B2 (en) 2013-05-17 2018-02-06 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US9895349B2 (en) 2013-04-03 2018-02-20 Janssen Sciences Ireland Us N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10071961B2 (en) 2013-10-23 2018-09-11 Janssen Sciences Ireland Uc Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10077239B2 (en) 2015-09-29 2018-09-18 Novira Therapeutics, Inc. Crystalline forms of a hepatitis B antiviral agent
US10125094B2 (en) 2013-02-28 2018-11-13 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10213420B2 (en) 2014-02-05 2019-02-26 Novira Therapeutics, Inc. Combination therapy for treatment of HBV infections
US10392349B2 (en) 2014-01-16 2019-08-27 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US10441589B2 (en) 2016-04-15 2019-10-15 Novira Therapeutics, Inc. Combinations and methods comprising a capsid assembly inhibitor
US10450270B2 (en) 2013-07-25 2019-10-22 Janssen Sciences Ireland Uc Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10537580B2 (en) 2015-03-19 2020-01-21 Novira Therapeutics, Inc. Azocane and azonane derivatives and methods of treating hepatitis B infections
US10676429B2 (en) 2012-08-28 2020-06-09 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10875876B2 (en) 2015-07-02 2020-12-29 Janssen Sciences Ireland Uc Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10973801B2 (en) 2018-03-14 2021-04-13 Janssen Sciences Ireland Unlimited Company Capsid assembly modulator dosing regimen
WO2021108628A1 (fr) 2019-11-25 2021-06-03 Alkermes, Inc. Composés macrocycliques substitués et méthodes de traitement associées
US11028048B2 (en) 2019-01-31 2021-06-08 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof
US11034700B2 (en) 2017-03-08 2021-06-15 Takeda Pharmaceutical Company Limited Substituted pyrrolidine compound and use thereof
US11059780B2 (en) 2017-03-08 2021-07-13 Takeda Pharmaceutical Company Limited Substituted pyrrolidine compound and use thereof
US11078193B2 (en) 2014-02-06 2021-08-03 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US11096931B2 (en) 2019-02-22 2021-08-24 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases
US11319286B2 (en) 2017-08-03 2022-05-03 Takeda Pharmaceutical Company Limited Heterocyclic compound and application thereof
WO2022140317A1 (fr) 2020-12-21 2022-06-30 Alkermes, Inc. Composés pipéridino substitués et procédés de traitement associés
WO2022140316A1 (fr) 2020-12-21 2022-06-30 Alkermes, Inc. Composés macrocycliques substitués et procédés de traitement associés
US11440883B2 (en) 2017-08-03 2022-09-13 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof
WO2022232025A1 (fr) 2021-04-26 2022-11-03 Alkermes, Inc. Composés macrocycliques d'amide substitués ayant une activité agoniste du récepteur de l'orexine 2
US11491148B2 (en) 2019-05-06 2022-11-08 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases
WO2022251304A1 (fr) 2021-05-26 2022-12-01 Alkerme, Inc. Composés macrocycliques de carbamate substitués et méthodes de traitement associées
WO2022251302A1 (fr) 2021-05-26 2022-12-01 Alkermes, Inc. Composés macrocycliques bicycliques fusionnés substitués et méthodes de traitement associées
US11655241B2 (en) 2018-06-29 2023-05-23 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof
US11673867B2 (en) 2017-12-12 2023-06-13 University Of Tsukuba Sulfonamide derivative or pharmaceutically acceptable acid-addition salt

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Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9676747B2 (en) 2011-12-21 2017-06-13 Novira Therapeutics, Inc. Hepatitis B antiviral agents
US9751857B2 (en) 2011-12-21 2017-09-05 Novira Therapeutics, Inc. Hepatitis B antiviral agents
US10196376B2 (en) 2011-12-21 2019-02-05 Novira Therapeutics, Inc. Hepatitis B antiviral agents
US10995064B2 (en) 2012-08-28 2021-05-04 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10676429B2 (en) 2012-08-28 2020-06-09 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10125094B2 (en) 2013-02-28 2018-11-13 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10941113B2 (en) 2013-02-28 2021-03-09 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10398677B2 (en) 2013-04-03 2019-09-03 Janssen Sciences Ireland Uc N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US9895349B2 (en) 2013-04-03 2018-02-20 Janssen Sciences Ireland Us N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10457638B2 (en) 2013-05-17 2019-10-29 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US9884818B2 (en) 2013-05-17 2018-02-06 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10450270B2 (en) 2013-07-25 2019-10-22 Janssen Sciences Ireland Uc Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10071961B2 (en) 2013-10-23 2018-09-11 Janssen Sciences Ireland Uc Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10377709B2 (en) 2013-10-23 2019-08-13 Janssen Sciences Ireland Uc Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10392349B2 (en) 2014-01-16 2019-08-27 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US9873671B2 (en) 2014-01-16 2018-01-23 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US10213420B2 (en) 2014-02-05 2019-02-26 Novira Therapeutics, Inc. Combination therapy for treatment of HBV infections
US10632112B2 (en) 2014-02-05 2020-04-28 Novira Therapeutics, Inc. Combination therapy for treatment of HBV infections
US11078193B2 (en) 2014-02-06 2021-08-03 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
EP3029024A1 (fr) * 2014-12-02 2016-06-08 Ferrer Internacional, S.A. Composés de 2-(2-aminophénoxy)-3-chloronaphthalène-1,4-dione présentant une activité d'agoniste du récepteur d'orexine 2
US10537580B2 (en) 2015-03-19 2020-01-21 Novira Therapeutics, Inc. Azocane and azonane derivatives and methods of treating hepatitis B infections
US10875876B2 (en) 2015-07-02 2020-12-29 Janssen Sciences Ireland Uc Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10077239B2 (en) 2015-09-29 2018-09-18 Novira Therapeutics, Inc. Crystalline forms of a hepatitis B antiviral agent
US10508083B2 (en) 2016-02-04 2019-12-17 Takeda Pharmaceutical Company Limited Substituted piperidine compound and use thereof
US10898737B2 (en) 2016-02-04 2021-01-26 Takeda Pharmaceutical Company Limited Substituted piperidine compound and use thereof
EP3984994A1 (fr) 2016-02-04 2022-04-20 Takeda Pharmaceutical Company Limited Composé de pipéridine substituée et son utilisation
WO2017135306A1 (fr) 2016-02-04 2017-08-10 Takeda Pharmaceutical Company Limited Composé de pipéridine substituée et son utilisation
US11292766B2 (en) 2016-02-04 2022-04-05 Takeda Pharmaceutical Company Limited Substituted piperidine compound and use thereof
US10287305B2 (en) 2016-02-04 2019-05-14 Takeda Pharmaceutical Company Limited Substituted piperidine compound and use thereof
US10441589B2 (en) 2016-04-15 2019-10-15 Novira Therapeutics, Inc. Combinations and methods comprising a capsid assembly inhibitor
US11129834B2 (en) 2016-04-15 2021-09-28 Novira Therapeutics, Inc. Combinations and methods comprising a capsid assembly inhibitor
US11059780B2 (en) 2017-03-08 2021-07-13 Takeda Pharmaceutical Company Limited Substituted pyrrolidine compound and use thereof
US11034700B2 (en) 2017-03-08 2021-06-15 Takeda Pharmaceutical Company Limited Substituted pyrrolidine compound and use thereof
US11319286B2 (en) 2017-08-03 2022-05-03 Takeda Pharmaceutical Company Limited Heterocyclic compound and application thereof
US11440883B2 (en) 2017-08-03 2022-09-13 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof
US11673867B2 (en) 2017-12-12 2023-06-13 University Of Tsukuba Sulfonamide derivative or pharmaceutically acceptable acid-addition salt
US10973801B2 (en) 2018-03-14 2021-04-13 Janssen Sciences Ireland Unlimited Company Capsid assembly modulator dosing regimen
US11655241B2 (en) 2018-06-29 2023-05-23 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof
US11028048B2 (en) 2019-01-31 2021-06-08 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof
US11096931B2 (en) 2019-02-22 2021-08-24 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases
US11491148B2 (en) 2019-05-06 2022-11-08 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases
WO2021108628A1 (fr) 2019-11-25 2021-06-03 Alkermes, Inc. Composés macrocycliques substitués et méthodes de traitement associées
WO2022140317A1 (fr) 2020-12-21 2022-06-30 Alkermes, Inc. Composés pipéridino substitués et procédés de traitement associés
WO2022140316A1 (fr) 2020-12-21 2022-06-30 Alkermes, Inc. Composés macrocycliques substitués et procédés de traitement associés
WO2022232025A1 (fr) 2021-04-26 2022-11-03 Alkermes, Inc. Composés macrocycliques d'amide substitués ayant une activité agoniste du récepteur de l'orexine 2
WO2022251304A1 (fr) 2021-05-26 2022-12-01 Alkerme, Inc. Composés macrocycliques de carbamate substitués et méthodes de traitement associées
WO2022251302A1 (fr) 2021-05-26 2022-12-01 Alkermes, Inc. Composés macrocycliques bicycliques fusionnés substitués et méthodes de traitement associées

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