FR3063079B1 - Derives sulfonamides hydroxyles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t) - Google Patents

Derives sulfonamides hydroxyles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t) Download PDF

Info

Publication number
FR3063079B1
FR3063079B1 FR1751310A FR1751310A FR3063079B1 FR 3063079 B1 FR3063079 B1 FR 3063079B1 FR 1751310 A FR1751310 A FR 1751310A FR 1751310 A FR1751310 A FR 1751310A FR 3063079 B1 FR3063079 B1 FR 3063079B1
Authority
FR
France
Prior art keywords
gamma
sulfonamide derivatives
retinoid
hydroxylated
orphan receptor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
FR1751310A
Other languages
English (en)
Other versions
FR3063079A1 (fr
Inventor
Branislav Musicki
Gilles Ouvry
Etienne Thoreau
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Galderma Research and Development SNC
Original Assignee
Galderma Research and Development SNC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Galderma Research and Development SNC filed Critical Galderma Research and Development SNC
Priority to FR1751310A priority Critical patent/FR3063079B1/fr
Priority to PCT/EP2018/053934 priority patent/WO2018149991A1/fr
Publication of FR3063079A1 publication Critical patent/FR3063079A1/fr
Application granted granted Critical
Publication of FR3063079B1 publication Critical patent/FR3063079B1/fr
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D309/06—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide 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
    • C07C311/44—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 a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

La présente invention concerne des dérivés sulfonamides particuliers, leurs sels d'addition pharmaceutiquement acceptables leurs hydrates et/ou leurs solvates ainsi que leur utilisation en tant qu'agoniste inverse du récepteur gamma orphelin associé aux rétinoïdes RORyt. L'invention est également relative à une composition pharmaceutique comprenant de tels composés ainsi que son utilisation pour le traitement par voie topique et/ou orale des maladies inflammatoires médiées par les récepteurs RORyt, notamment l'acné, le psoriasis et/ou la dermatite atopique.
FR1751310A 2017-02-17 2017-02-17 Derives sulfonamides hydroxyles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t) Expired - Fee Related FR3063079B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FR1751310A FR3063079B1 (fr) 2017-02-17 2017-02-17 Derives sulfonamides hydroxyles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t)
PCT/EP2018/053934 WO2018149991A1 (fr) 2017-02-17 2018-02-16 Dérivés sulfonamides hydroxylés en tant qu'agonistes inverses du récepteur gamma orphelin associé aux rétinoïdes ror gamma (t)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1751310A FR3063079B1 (fr) 2017-02-17 2017-02-17 Derives sulfonamides hydroxyles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t)
FR1751310 2017-02-17

Publications (2)

Publication Number Publication Date
FR3063079A1 FR3063079A1 (fr) 2018-08-24
FR3063079B1 true FR3063079B1 (fr) 2019-03-22

Family

ID=58707768

Family Applications (1)

Application Number Title Priority Date Filing Date
FR1751310A Expired - Fee Related FR3063079B1 (fr) 2017-02-17 2017-02-17 Derives sulfonamides hydroxyles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t)

Country Status (2)

Country Link
FR (1) FR3063079B1 (fr)
WO (1) WO2018149991A1 (fr)

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012100732A1 (fr) 2011-01-24 2012-08-02 Glaxo Group Limited Modulateurs des récepteurs orphelins gamma apparentés au récepteur des rétinoïdes, composition les contenant et utilisations associées
JP5209761B2 (ja) 2011-06-29 2013-06-12 株式会社ユニバンス 太陽追尾装置
WO2013085890A1 (fr) 2011-12-06 2013-06-13 Glaxo Group Limited Méthodes thérapeutiques
US20130190356A1 (en) 2011-12-22 2013-07-25 Genentech, Inc. Benzyl sulfonamide derivatives as rorc modulators
US9216988B2 (en) 2011-12-22 2015-12-22 Genentech, Inc. Benzyl sulfonamide derivatives as RORc modulators
GB201207406D0 (en) 2012-04-27 2012-06-13 Glaxo Group Ltd Novel compounds
JP6182594B2 (ja) * 2012-04-27 2017-08-16 グラクソ グループ リミテッドＧｌａｘｏ Ｇｒｏｕｐ Ｌｉｍｉｔｅｄ 新規化合物
RU2014149149A (ru) 2012-05-08 2016-07-10 Мерк Шарп И Доум Корп. БИЦИКЛИЧЕСКИЕ СУЛЬФОНОВЫЕ СОЕДИНЕНИЯ ДЛЯ ИНГИБИРОВАНИЯ RORгамма АКТИВНОСТИ И ЛЕЧЕНИЯ ЗАБОЛЕВАНИЯ
AR091654A1 (es) 2012-07-02 2015-02-18 Biogen Idec Inc COMPUESTOS QUE CONTIENEN BIARILO COMO AGONISTAS INVERSOS DE RECEPTORES ROR-g
JP2016502987A (ja) 2012-12-10 2016-02-01 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ ＲＯＲｃモジュレーターとしてのベンジルスルホンアミド誘導体
FR3030518B1 (fr) * 2014-12-19 2018-03-23 Galderma Research & Development Derives sulfonamides en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t)
FR3030516B1 (fr) 2014-12-19 2019-12-27 Galderma Research & Development Derives sulfonamides bicycles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t)

Also Published As

Publication number Publication date
FR3063079A1 (fr) 2018-08-24
WO2018149991A1 (fr) 2018-08-23

Similar Documents

Publication Publication Date Title
FR3030516B1 (fr) Derives sulfonamides bicycles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t)
MA40111B1 (fr) Dérivés du tétrahydronaphtalène inhibant la protéine mcl-1
SA518392101B1 (ar) ROR-Gamma مشتقات البنزيميدازول في صورة مُعدلات لـ
MA45598B1 (fr) Stéroles 24-hydroxylés substitués en position 11 pour le traitement des maladies liées au récepteur nmda
MA41051B1 (fr) Modulateurs du régulateur de conductance transmembranaire de la mucoviscidose
MA42678B1 (fr) Nouveaux analogues nucléosidiques substitués à cycle aromatique bicyclique 6-6 pour une utilisation en tant qu'inhibiteurs de prmt5
CO2020012060A2 (es) Inhibidores de la arginasa
MA53399B1 (fr) Pyrazoles substitués en tant qu`inhibiteurs de la kallicréine plasmatique humaine
MA38398B1 (fr) Composés biaryle amides en tant qu'inhibiteurs de kinase
CO2019010078A2 (es) Compuestos de pirimidinil-pyridiloxi-naftil y métodos para tratar enfermedades y trastornos relacionados con ire1
ECSP11010796A (es) Compuestos de pirimidina, composiciones y métodos de uso
MA39725B1 (fr) Compositions pharmaceutiques de composés thérapeutiquement actifs
MA28435B1 (fr) Composes d'indazole-carboxamide en tant qu'agonistes de recepteur 5-ht4
MX2019003397A (es) Metodos para tratar trastornos mitocondriales y metabolicos.
MA38482A1 (fr) Dérivés de pyridin-4-yle agonistes du recepteur de la sphingosine-1-phosphate utilises pour traiter, par ex. Syndromes auto-immuns, sclerose en plaques, colite ulcereuse, psoriasis et migraine
MA33419B1 (fr) Composés et compositions pour le traitement de maladies parasitaires
PA8807801A1 (es) Inhibidores de cinesina como productos terapeuticos para el cancer
BR112018015125A2 (pt) ?derivado de amina cíclica, medicamento, antagonista do receptor órfão ¿ relacionado com retinoide, e, agente terapêutico ou agente preventivo?
MA38425B1 (fr) Composés bicycliques pour une utilisation comme agonistes selectifs pour le recepteur s1p1
DOP2022000130A (es) Derivados de benzimidazol
SG11201805791RA (en) COMPOSITION FOR INCREASING EXPRESSION OF PGC-1α
MA38678A1 (fr) Dérivés nucléosidiques 4'-azido, 3'désoxy-3'-fluoro substitués
FR3063079B1 (fr) Derives sulfonamides hydroxyles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t)
MA39253B1 (fr) Composés hétéroaryle bicycliques substitués utilisés comme agonistes de rxr
MA39750B1 (fr) Dérivés d'acide aza-indol-acétique et leur utilisation comme modulateurs des récepteurs de la prostaglandine d2

Legal Events

Date Code Title Description
PLFP Fee payment

Year of fee payment: 2

PLSC Search report ready

Effective date: 20180824

PLFP Fee payment

Year of fee payment: 3

ST Notification of lapse

Effective date: 20201005