WO2005003097A1 - Cis-2,4,5-triaryl-imidazolines - Google Patents

Cis-2,4,5-triaryl-imidazolines Download PDF

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Publication number
WO2005003097A1
WO2005003097A1 PCT/EP2004/006176 EP2004006176W WO2005003097A1 WO 2005003097 A1 WO2005003097 A1 WO 2005003097A1 EP 2004006176 W EP2004006176 W EP 2004006176W WO 2005003097 A1 WO2005003097 A1 WO 2005003097A1
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WO
WIPO (PCT)
Prior art keywords
phenyl
trifluoromethyl
bis
chloro
dihydro
Prior art date
Application number
PCT/EP2004/006176
Other languages
English (en)
Inventor
Gregory Jay Haley
Norman Kong
Emily Aijun Liu
Klaus B. Simonsen
Binh Thanh Vu
Stephen Evan Webber
Original Assignee
F. Hoffmann-La Roche Ag
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 F. Hoffmann-La Roche Ag filed Critical F. Hoffmann-La Roche Ag
Priority to AU2004254187A priority Critical patent/AU2004254187A1/en
Priority to MXPA05013279A priority patent/MXPA05013279A/es
Priority to JP2006515856A priority patent/JP2006527712A/ja
Priority to BRPI0411841-3A priority patent/BRPI0411841A/pt
Priority to EP04739704A priority patent/EP1638942A1/fr
Priority to CA002528119A priority patent/CA2528119A1/fr
Publication of WO2005003097A1 publication Critical patent/WO2005003097A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/22—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

Definitions

  • Ri 8 is selected from the group consisting of lower alkoxy, cyano, trifluoromethyl, heterocycle and hydroxyl;
  • R is selected from the group consisting of
  • R 5 is selected from the group consisting of oxo, heteroaryl, aryl substituted by a substituent selected from lower alkoxy and fluoro,
  • N-lower alkyl substituted by R ⁇ 8 heterocycle and heterocycle substituted by one or two substituents selected from the group consisting of hydroxy, alkoxy, trifluoromethyl, C(O)-lower alkyl, C(O)-NH 2 , C(O)-N-lower alkyl, lower alkyl substituted by hydroxy and oxo;
  • R17 is selected from the group consisting of
  • heterocycle elected from the group consisting of
  • Xi and X 2 are chloro, X 3 is ethoxy or sopropoxy, the trifluoromethyl group is meta to the imidazoline ring, and R is C(O)- ?iperazine substituted by R 5 .
  • “Pharmaceutically acceptable salt” refers to conventional acid-addition salts or base- addition salts that retain the biological effectiveness and properties of the compounds of the present invention and are formed from suitable non-toxic organic or inorganic acids or organic or inorganic bases.
  • Sample acid-addition salts include those derived from inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, sulfamic acid, phosphoric acid and nitric acid, and those derived from organic acids such as p-toluenesulfonic acid, salicylic acid, methanesulfonic acid, oxalic acid, succinic acid, citric acid, malic acid, lactic acid, fumaric acid, and the like.
  • the compound of formula 9 can react with an appropriately protected piperidine to afford a compound of formula 15 after deprotection.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La présente invention concerne des composés de formule (I) qui ont les désignations mentionnées, ainsi que des sels et des esters de ceux-ci, acceptables d'un point de vue pharmaceutique. Ces composés inhibent l'interaction d'une protéine MDM2 avec un peptide de type p53 et présentent une activité antiprolifération.
PCT/EP2004/006176 2003-06-17 2004-06-08 Cis-2,4,5-triaryl-imidazolines WO2005003097A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2004254187A AU2004254187A1 (en) 2003-06-17 2004-06-08 Cis-2,4,5-triaryl-imidazolines
MXPA05013279A MXPA05013279A (es) 2003-06-17 2004-06-08 Cis-2,4,5-triaril-imidazolinas.
JP2006515856A JP2006527712A (ja) 2003-06-17 2004-06-08 シス−２，４，５−トリアリール−イミダゾリン
BRPI0411841-3A BRPI0411841A (pt) 2003-06-17 2004-06-08 cis-2,4,5-triaril-imidazolinas
EP04739704A EP1638942A1 (fr) 2003-06-17 2004-06-08 Cis-2,4,5-triaryl-imidazolines
CA002528119A CA2528119A1 (fr) 2003-06-17 2004-06-08 Cis-2,4,5-triarylimidazolines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US47935103P 2003-06-17 2003-06-17
US60/479,351 2003-06-17

Publications (1)

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WO2005003097A1 true WO2005003097A1 (fr) 2005-01-13

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EP (1) EP1638942A1 (fr)
JP (1) JP2006527712A (fr)
KR (1) KR100768021B1 (fr)
CN (1) CN100465163C (fr)
AR (1) AR044703A1 (fr)
AU (1) AU2004254187A1 (fr)
BR (1) BRPI0411841A (fr)
CA (1) CA2528119A1 (fr)
CL (1) CL2004001484A1 (fr)
MX (1) MXPA05013279A (fr)
RU (1) RU2319696C2 (fr)
TW (1) TW200510387A (fr)
WO (1) WO2005003097A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008072655A1 (fr) 2006-12-14 2008-06-19 Daiichi Sankyo Company, Limited Dérivés d'imidazothiazole
JP2008533073A (ja) * 2005-03-16 2008-08-21 エフ．ホフマン−ラ ロシュ アーゲー シス−２，４，５−トリアリール−イミダゾリン及びそれらの抗癌薬としての使用
WO2009151069A1 (fr) 2008-06-12 2009-12-17 第一三共株式会社 Dérivé d’imidazothiazole ayant une structure cyclique de 4,7-diazaspiro[2.5]octane
WO2010082612A1 (fr) 2009-01-16 2010-07-22 第一三共株式会社 Dérivé d'imidazothiazole comprenant une structure de noyau proline
JP4870778B2 (ja) * 2005-12-01 2012-02-08 エフ．ホフマン−ラ ロシュ アーゲー 抗ガン剤として使用されるｐ５３およびｍｄｍ２タンパク質間の相互作用の阻害剤としての２，４，５−トリフェニルイミダゾリン誘導体
US8114095B2 (en) * 2006-11-10 2012-02-14 Bausch & Lomb Incorporated Intraocular lens injection apparatus and method
WO2013054153A1 (fr) 2011-10-11 2013-04-18 INSERM (Institut National de la Santé et de la Recherche Médicale) Composés de nutline pour une utilisation dans le traitement de l'hypertension artérielle pulmonaire
WO2017201449A1 (fr) 2016-05-20 2017-11-23 Genentech, Inc. Conjugués anticorps-protac et procédés d'utilisation
WO2023056069A1 (fr) 2021-09-30 2023-04-06 Angiex, Inc. Conjugués agent de dégradation-anticorps et leurs procédés d'utilisation
RU2809688C1 (ru) * 2022-10-03 2023-12-14 Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) Новые азотзамещенные 2,4,5-три(метоксифенил) цис-имидазолины, способ их получения и применения

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7625895B2 (en) * 2007-04-12 2009-12-01 Hoffmann-Le Roche Inc. Diphenyl-dihydro-imidazopyridinones
IT1396520B1 (it) 2009-12-10 2012-12-14 Nuovo Pignone Spa Accoppiamento per bilanciamento rotore

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0433682A2 (fr) * 1989-11-22 1991-06-26 Marion Merrell Dow Inc. Utilisation de 2,4,5-tri(4-méthoxyphényl)-4,5-dihydroimidazole pour le traitement du cancer
WO2002020017A2 (fr) * 2000-09-04 2002-03-14 Merck Patent Gmbh Utilisation de l'ectoine ou de derives de l'ectoine pour la stabilisation du p53
WO2003051359A1 (fr) * 2001-12-18 2003-06-26 F.Hoffmann-La Roche Ag Cis-2,4,5- triphenyl-imidazolines et leurs utilisations dans le traitement des tumeurs

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0433682A2 (fr) * 1989-11-22 1991-06-26 Marion Merrell Dow Inc. Utilisation de 2,4,5-tri(4-méthoxyphényl)-4,5-dihydroimidazole pour le traitement du cancer
WO2002020017A2 (fr) * 2000-09-04 2002-03-14 Merck Patent Gmbh Utilisation de l'ectoine ou de derives de l'ectoine pour la stabilisation du p53
WO2003051359A1 (fr) * 2001-12-18 2003-06-26 F.Hoffmann-La Roche Ag Cis-2,4,5- triphenyl-imidazolines et leurs utilisations dans le traitement des tumeurs

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SEUNG HOON CHEON ET AL: "Synthesis and Structure-Activity Relationship Studies of 2,3-Dihydroimidazo[2,1-a]isoquinoline Analogs as Antitumor Agents", ARCHIVES OF PHARMACAL RESEARCH, vol. 20, no. 2, 1997, NATIONAL FISHERIES UNIVERSITY, PUSAN, KOREA, pages 138 - 143, XP009036613 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008533073A (ja) * 2005-03-16 2008-08-21 エフ．ホフマン−ラ ロシュ アーゲー シス−２，４，５−トリアリール−イミダゾリン及びそれらの抗癌薬としての使用
JP4870778B2 (ja) * 2005-12-01 2012-02-08 エフ．ホフマン−ラ ロシュ アーゲー 抗ガン剤として使用されるｐ５３およびｍｄｍ２タンパク質間の相互作用の阻害剤としての２，４，５−トリフェニルイミダゾリン誘導体
US8114095B2 (en) * 2006-11-10 2012-02-14 Bausch & Lomb Incorporated Intraocular lens injection apparatus and method
WO2008072655A1 (fr) 2006-12-14 2008-06-19 Daiichi Sankyo Company, Limited Dérivés d'imidazothiazole
WO2009151069A1 (fr) 2008-06-12 2009-12-17 第一三共株式会社 Dérivé d’imidazothiazole ayant une structure cyclique de 4,7-diazaspiro[2.5]octane
WO2010082612A1 (fr) 2009-01-16 2010-07-22 第一三共株式会社 Dérivé d'imidazothiazole comprenant une structure de noyau proline
US8404691B2 (en) 2009-01-16 2013-03-26 Daiichi Sankyo Company, Limited Imidazothiazole derivatives having proline ring structure
WO2013054153A1 (fr) 2011-10-11 2013-04-18 INSERM (Institut National de la Santé et de la Recherche Médicale) Composés de nutline pour une utilisation dans le traitement de l'hypertension artérielle pulmonaire
WO2017201449A1 (fr) 2016-05-20 2017-11-23 Genentech, Inc. Conjugués anticorps-protac et procédés d'utilisation
WO2023056069A1 (fr) 2021-09-30 2023-04-06 Angiex, Inc. Conjugués agent de dégradation-anticorps et leurs procédés d'utilisation
RU2809688C1 (ru) * 2022-10-03 2023-12-14 Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) Новые азотзамещенные 2,4,5-три(метоксифенил) цис-имидазолины, способ их получения и применения

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RU2319696C2 (ru) 2008-03-20
CN1809538A (zh) 2006-07-26
CA2528119A1 (fr) 2005-01-13
AR044703A1 (es) 2005-09-21
KR20060021902A (ko) 2006-03-08
JP2006527712A (ja) 2006-12-07
AU2004254187A1 (en) 2005-01-13
EP1638942A1 (fr) 2006-03-29
CL2004001484A1 (es) 2005-05-27
TW200510387A (en) 2005-03-16
KR100768021B1 (ko) 2007-10-18
MXPA05013279A (es) 2006-03-09
RU2006100730A (ru) 2006-08-10
CN100465163C (zh) 2009-03-04
BRPI0411841A (pt) 2006-08-08

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