WO2008111632A1 - Glucocorticoid receptor agonist composed of 2,2,4-trimethyl-6-phenyl-1,2-dihydroquinoline derivative - Google Patents

Glucocorticoid receptor agonist composed of 2,2,4-trimethyl-6-phenyl-1,2-dihydroquinoline derivative Download PDF

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Publication number
WO2008111632A1
WO2008111632A1 PCT/JP2008/054568 JP2008054568W WO2008111632A1 WO 2008111632 A1 WO2008111632 A1 WO 2008111632A1 JP 2008054568 W JP2008054568 W JP 2008054568W WO 2008111632 A1 WO2008111632 A1 WO 2008111632A1
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receptor agonist
glucocorticoid receptor
trimethyl
phenyl
represent
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PCT/JP2008/054568
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French (fr)
Japanese (ja)
Inventor
Masatomo Kato
Miwa Takai
Takahiro Matsuyama
Tatsuji Kurose
Yumi Hagiwara
Mamoru Matsuda
Toshiyuki Mori
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Santen Pharmaceutical Co., Ltd.
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Publication of WO2008111632A1 publication Critical patent/WO2008111632A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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Abstract

Disclosed is a glucocorticoid receptor agonist composed of a 2,2,4-trimethyl-6-phenyl-1,2-dihydroquinoline derivative. Also disclosed is a novel pharmacological activity of the agonist. Specifically disclosed is a glucocorticoid receptor agonist composed of a compound represented by the formula (1) below or a salt thereof. [In the formulae below, R1 represents a group represented by the general formula (2a), (3a), (4a) or (5a); R2 and R3 may be the same or different and represent a hydrogen atom, a halogen atom, a lower alkyl group or the like; R4 represents a lower alkyl group; R5, R6, R7 and R8 represent a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group or the like; and m, n, p and q represent 0, 1 or 2.]
PCT/JP2008/054568 2007-03-13 2008-03-13 Glucocorticoid receptor agonist composed of 2,2,4-trimethyl-6-phenyl-1,2-dihydroquinoline derivative WO2008111632A1 (en)

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JP2007-063010 2007-03-13
JP2007063010 2007-03-13

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2085389A1 (en) * 2006-11-14 2009-08-05 Santen Pharmaceutical Co., Ltd Novel 1,2-dihydroquinoline derivative having (substituted phenyl or substituted heterocyclic) carbonyloxy lower alkyl group and ester-introduced phenyl group as substituents
WO2009139361A1 (en) * 2008-05-12 2009-11-19 参天製薬株式会社 Glucocorticoid receptor agonist composed of 2,2,4-trimethyl-6-phenyl-1,2-dihydroquinoline derivative having substituted oxy group
WO2010029986A1 (en) * 2008-09-12 2010-03-18 参天製薬株式会社 Glucocorticoid receptor agonist comprising novel 1,2,3,4-tetrahydroquinoxaline derivative containing phenyl group having sulfonic acid ester structure introduced therein as substituent
US8017775B2 (en) 2005-09-14 2011-09-13 Santen Pharmaceutical Co., Ltd. 1-2-dihydroquinoline derivative having glucocorticoid receptor binding activity
US8193187B2 (en) 2007-05-29 2012-06-05 Santen Pharmaceutical Co., Ltd. 1,2,3,4-tetrahydroquinoxaline compound with a phenyl group substituent having a sulfonic acid ester structure or a sulfonic acid amide structure introduced therein and having glucocorticoid receptor-binding activity
WO2013108921A1 (en) * 2012-01-20 2013-07-25 参天製薬株式会社 Industrial process for preparation of 1,2-dihydroquinoline derivative or a salt thereof, and intermediate for preparation thereof
US8551991B2 (en) 2006-03-14 2013-10-08 Santen Pharmaceutical Co., Ltd. 1,2,3,4-tetrahydroquinoxaline derivative having glucocorticoid receptor binding activity
WO2018230713A1 (en) 2017-06-16 2018-12-20 学校法人同志社 Compounds having caspase inhibitory activity, pharmaceutical agent containing said compounds and for treating or preventing corneal endothelial symptoms, disorders, or diseases, and application of said pharmaceutical agent
US11433090B2 (en) 2017-06-16 2022-09-06 The Doshisha mTOR-inhibitor-containing medicine for treating or preventing ophthalmic symptoms, disorders, or diseases, and application thereof

Citations (4)

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Publication number Priority date Publication date Assignee Title
JPH10510840A (en) * 1994-12-22 1998-10-20 リガンド・ファーマシューティカルズ・インコーポレイテッド Steroid receptor modulator compounds and methods
JP2006504678A (en) * 2002-08-21 2006-02-09 ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド Glucocorticoid mimetics, process for producing the same, pharmaceutical composition thereof, and use thereof
WO2006019716A1 (en) * 2004-07-14 2006-02-23 Ligand Pharmaceuticals, Inc. Intracellular receptor modulator compounds and methods
WO2007032556A1 (en) * 2005-09-14 2007-03-22 Santen Pharmaceutical Co., Ltd. Novel 1-2-dihydroquinoline derivative having glucocorticoid receptor binding activity

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10510840A (en) * 1994-12-22 1998-10-20 リガンド・ファーマシューティカルズ・インコーポレイテッド Steroid receptor modulator compounds and methods
JP2006504678A (en) * 2002-08-21 2006-02-09 ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド Glucocorticoid mimetics, process for producing the same, pharmaceutical composition thereof, and use thereof
WO2006019716A1 (en) * 2004-07-14 2006-02-23 Ligand Pharmaceuticals, Inc. Intracellular receptor modulator compounds and methods
WO2007032556A1 (en) * 2005-09-14 2007-03-22 Santen Pharmaceutical Co., Ltd. Novel 1-2-dihydroquinoline derivative having glucocorticoid receptor binding activity

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8420635B2 (en) 2005-09-14 2013-04-16 Santen Pharmaceutical Co., Ltd. Method for preventing or treating a glucocorticoid receptor-related disease
US8017775B2 (en) 2005-09-14 2011-09-13 Santen Pharmaceutical Co., Ltd. 1-2-dihydroquinoline derivative having glucocorticoid receptor binding activity
US8551991B2 (en) 2006-03-14 2013-10-08 Santen Pharmaceutical Co., Ltd. 1,2,3,4-tetrahydroquinoxaline derivative having glucocorticoid receptor binding activity
US8975256B2 (en) 2006-03-14 2015-03-10 Santen Pharmaceutical Co., Ltd. 1,2,3,4-tetrahydroquinoxaline compounds having glucocorticoid receptor binding activity
US8008496B2 (en) 2006-11-14 2011-08-30 Santen Pharmaceutical Co., Ltd. 1,2-dihydroquinoline derivative having substituted phenylchalcogeno lower alkyl group and ester-introduced phenyl group as substituents
EP2085387A4 (en) * 2006-11-14 2010-12-15 Santen Pharmaceutical Co Ltd Novel 1,2-dihydroquinoline derivative having substituted phenylchalcogeno lower alkyl group and ester-introduced phenyl group as substituents
EP2085389A4 (en) * 2006-11-14 2010-12-15 Santen Pharmaceutical Co Ltd Novel 1,2-dihydroquinoline derivative having (substituted phenyl or substituted heterocyclic) carbonyloxy lower alkyl group and ester-introduced phenyl group as substituents
EP2085388A4 (en) * 2006-11-14 2010-12-15 Santen Pharmaceutical Co Ltd Novel 1,2-dihydroquinoline derivative having substituted phenylamino lower alkyl group and ester-introduced phenyl group as substituents
US8580784B2 (en) 2006-11-14 2013-11-12 Santen Pharmaceutical Co., Ltd. Method for treating a disease related to the glucocorticoid receptor
US8008498B2 (en) 2006-11-14 2011-08-30 Santen Pharmaceutical Co., Ltd. 1,2-dihydroquinoline derivative having substituted phenylamino lower alkyl group and ester-introduced phenyl group as substituents
US8008497B2 (en) 2006-11-14 2011-08-30 Santen Pharmaceutical Co., Ltd. 1,2-dihydroquinoline derivative having (substituted phenyl or substituted heterocyclic) carbonyloxy lower alkyl group and ester-introduced phenyl group as substituents
EP2085387A1 (en) * 2006-11-14 2009-08-05 Santen Pharmaceutical Co., Ltd Novel 1,2-dihydroquinoline derivative having substituted phenylchalcogeno lower alkyl group and ester-introduced phenyl group as substituents
EP2085389A1 (en) * 2006-11-14 2009-08-05 Santen Pharmaceutical Co., Ltd Novel 1,2-dihydroquinoline derivative having (substituted phenyl or substituted heterocyclic) carbonyloxy lower alkyl group and ester-introduced phenyl group as substituents
EP2085388A1 (en) * 2006-11-14 2009-08-05 Santen Pharmaceutical Co., Ltd Novel 1,2-dihydroquinoline derivative having substituted phenylamino lower alkyl group and ester-introduced phenyl group as substituents
US8563551B2 (en) 2006-11-14 2013-10-22 Santen Pharmaceutical Co., Ltd. Method for preventing or treating a disease related to the glucocorticoid receptor
US8440660B2 (en) 2006-11-14 2013-05-14 Santen Pharmaceutical Co., Ltd. Method for treating a disease related to the glucocorticoid receptor
US8569493B2 (en) 2007-05-29 2013-10-29 Santen Pharmaceutical Co., Ltd. Method for treating a homeostasis-related disease or glaucoma by administering a 1,2,3,4-tetrahyroquinoxaline compound
US8193187B2 (en) 2007-05-29 2012-06-05 Santen Pharmaceutical Co., Ltd. 1,2,3,4-tetrahydroquinoxaline compound with a phenyl group substituent having a sulfonic acid ester structure or a sulfonic acid amide structure introduced therein and having glucocorticoid receptor-binding activity
US8426406B2 (en) 2008-05-12 2013-04-23 Santen Pharmaceutical Co., Ltd. Glucocorticoid receptor agonist comprising 2,2,4-trimethyl-6-phenyl-1,2-dihydroquinoline derivatives having substituted oxy group
EA019091B1 (en) * 2008-05-12 2014-01-30 Сантен Фармасьютикал Ко., Лтд. Glucocorticoid receptor agonist composed of 2,2,4-trimethyl-6-phenyl-1,2-dihydroquinoline derivative having substituted oxy group
WO2009139361A1 (en) * 2008-05-12 2009-11-19 参天製薬株式会社 Glucocorticoid receptor agonist composed of 2,2,4-trimethyl-6-phenyl-1,2-dihydroquinoline derivative having substituted oxy group
EA018420B1 (en) * 2008-09-12 2013-07-30 Сантен Фармасьютикал Ко., Лтд. Glucocorticoid receptor agonist comprising novel 1,2,3,4-tetrahydroquinoxaline derivatives containing phenyl group having sulfonic acid ester structure introduced therein as substituent
WO2010029986A1 (en) * 2008-09-12 2010-03-18 参天製薬株式会社 Glucocorticoid receptor agonist comprising novel 1,2,3,4-tetrahydroquinoxaline derivative containing phenyl group having sulfonic acid ester structure introduced therein as substituent
US8664221B2 (en) 2008-09-12 2014-03-04 Santen Pharmaceutical Co., Ltd. Method for treating an inflammatory disease by administering a 1,2,3,4- tetrahydroquinoxaline compound containing a phenyl group having a sulfonic acid ester structure introduced therein as a substituent
JP2013166752A (en) * 2012-01-20 2013-08-29 Santen Pharmaceut Co Ltd Industrial process for preparation of 1,2-dihydroquinoline derivative or salt thereof, and intermediate for preparation thereof
WO2013108921A1 (en) * 2012-01-20 2013-07-25 参天製薬株式会社 Industrial process for preparation of 1,2-dihydroquinoline derivative or a salt thereof, and intermediate for preparation thereof
CN104136432A (en) * 2012-01-20 2014-11-05 参天制药株式会社 Industrial process for preparation of 1,2-dihydroquinoline derivative or a salt thereof, and intermediate for preparation thereof
WO2018230713A1 (en) 2017-06-16 2018-12-20 学校法人同志社 Compounds having caspase inhibitory activity, pharmaceutical agent containing said compounds and for treating or preventing corneal endothelial symptoms, disorders, or diseases, and application of said pharmaceutical agent
US11433090B2 (en) 2017-06-16 2022-09-06 The Doshisha mTOR-inhibitor-containing medicine for treating or preventing ophthalmic symptoms, disorders, or diseases, and application thereof

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